LODHA WORLD SCHOOL, LSG

Chemistry Investigatory Project

To prepare β-naphthol methyl

ether by oxymethylation of
β- naphthol

Submitted to the CBSE for the fulfillment of requirement of AISSCE 2024-25

Guided by: Mrs. Suvarna Asadala (P.G Chemistry)

Mr. (Lab Assistant)

Submitted by:

Class: XII A

Roll no.:

Board roll no.:

 CERTIFICATE

This is to certify that Mr.____________________ , a student of

Class 12 has successfully completed the investigatory project on
the mentioned topic O-methylation of β-naphthol under the
guidance of Ms. Suvarna Asadala, Chemistry teacher during the
academic year 2024-25 in partial fulfilment of chemistry practical
examination by AISSCE, New Delhi.

Internal Examiner Signature External Examiner Signature

Ms. Suvarna Asadala

Date:
Place:
 ACKNOWLDEGMENT

I would take this opportunity to express my sincere thanks

and gratitude to my Chemistry teacher Ms. Suvarna Asadala
(PGT) as well as our principal Ms. Rashmirekha Saha for vital
support and guidance in completing this investigatory project.

I would also like to extend my gratitude and thanks to our

lab assistant Mr.Rajesh Shelar who has helped me in successful
completion of my project work.

I wish to express my heartiest gratitude to God, to my

family members, my classmates and all those who selflessly
devoted time for any help that was required.

XYZ
XII -PCB/PCM
 Index
Sr. no. Content Page no.
1 Aim 4
2 Objective 4
3 Introduction 5
4 Problem Question 6
5 Materials Required 7
6 Procedure 8
7 Observation 9
8 Mechanism 9
9 Calculation 10
10 Advantages and disadvantages 11
11 Precautions 12
12 Bibliography 13

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Aim
To prepare β-naphthol methyl ether by oxymethylation of β-naphthol

Objectives
1. β-Naphthol methyl ether, also called 2-methoxynaphthalene, is a stabilizer found
in gunpowder, particularly smokeless gunpowder.
2. It is soluble in alcohol, and weakly soluble in water and dipropylene glycol.
3. Studies have also been done on the anti-inflammatory effect of β-naphthol methyl
ether and on how it behaves in time-resolved resonance in the Raman studies.
4. Intermediate in the production of naproxen.
5. Used in perfumes to impart the scent of orange blossoms.
6. Cyclic ethers, such as tetrahydrofuran, are commonly used as organic solvents.

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Introduction
This experiment investigates the methylation
of 2-naphthol with dimethyl sulphate. The
volatility of the substrates, products, and co-
products allows the reaction to be performed
using a continuous-flow gas-phase setup at
ambient pressure.
β-naphthol methyl ether can be prepared by
oxy-methylation of β-naphthol with dimethyl
sulphate. It has a faint but persistent odour
and used to be a scented compound found in
soap and other products. The physical properties of β- β-naphthol (C10H8O)
naphthol methyl ether are as follows: C10H7-OH
Molecular weight: 158.20
Melting point: 70-74◦C

The production of fine chemicals through environmentally clean and economical

processes is an area of growing importance. Many of the processes used at present in the
fine chemicals industries are either non-catalytic or based on homogeneous catalysts,
which are difficult to recover and reuse. Solid inorganic catalysts, on the otherhand, are
easily separable and recyclable. Besides, these catalysts are often environmentally
friendly.
Heterogeneous catalysis over solid bases is another growing area of research. Many solid
bases have recently been found useful in the production of fine chemical. Alkali and
alkaline earth metal oxides, rare earth oxides, supported alkali metals (ions) and clay
minerals act as heterogeneous basic catalysts.
For this experiment, we use dimethyl-sulphate as the methylating agent. The by- product
salt formed after the reaction is a neutral salt, sodium sulphate and thus need not be
neutralized.
The process adopted here is ‘oxy-methylation’, or addition of methyl on oxygen of the
alcoholic functional group in β-naphthol. NaOH is used to provide a basic medium for
the reaction and to neutralize the H2SO4 formed. It can be considered as a type of
electrophillic substitution reaction as –CH3+ is an electrophile.

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Problem Question

What are the uses of β-naphthol methyl ether industrially?

• Nerolin II (2-ethoxynapthalene), aromatic ether, which is obtained from β-

naphthol methyl ether is used in perfumes for the scent of orange blossoms.
Due to its aromatic nature, it is also used in soap industry. It is also used as a
stabilizer in smokeless gunpowder.

What is the solubility of β-naphthol methyl ether?

• β-Naphthol methyl ether is soluble in alcohol and insoluble in water.

Is there any medical use of β-Naphthol methyl ether?

• Yes. Recent studies have shown that β-Naphthol methyl ether has anti-
inflammatory effects.

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Materials Required
Apparatus
Conical flask Measuring cylinder Centrifuge tube

Dropper Beaker Filter paper

Air oven Glass rod Ice bath setup

Centrifuge Watch glass

Chemicals and Reagents

NaOH pellets Distilled water

β-naphthol Dimethyl sulphate

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We observed the formation of solid product.
The yield obtained in mass is = 1.6g
Physical nature of product:
1. Appearance: Flaky solid
2. Colour: White
3. Solubility: Soluble in alcohol and weakly soluble in
water.
4. Odour: Sweet, floral orange smell
β-naphthol methyl ether (C11H10O)
C10H7-O-CH3
The Chemical reaction involved is:

Mechanism
Protonation of β-naphthol
H+ ion from alcohol group (-OH) of β-naphthol is dissociated.

Electrophile formation
CH3+ from Dimethyl sulfate is dissociated. SO42- is also a dissociated ion.

Bond cleavage of NaOH

Cation and anion Na+ and OH- are formed respectively.

Attack of electrophile on β-naphthol anion

CH3+ attacks oxygen in β-naphthol to form β-naphthol methyl ether

Formation of side products

Na+ attacks negatively charged SO42- to form sodium sulfate and OH- and H+ forms water.

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10 | P a g
e
Calculation
To calculate mass of NaOH for 15 mL 10w/v% NaOH solution
required w⁄v % × volume of solution
Mass of NaOH =
100
10 × 15 150
Mass of NaOH = = = 1.5g
100 100

To calculate percentage yield to determine efficiency of reaction

mass of product obtained × 100
Percent yield =
Theoretical yield
Supplied quantity = 2g
Theoretical yield
𝑚𝑜𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 𝑜ƒ 𝑝𝑟𝑜𝑑𝑢𝑐𝑡 × 𝑠𝑢𝑝𝑝𝑙i𝑒𝑑 𝑞𝑢𝑎𝑛𝑡i𝑡𝑦 𝑜ƒ 𝑟𝑒𝑎𝑐𝑡𝑎𝑛𝑡
=
𝑚𝑜𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 𝑜ƒ 𝑟𝑒𝑎𝑐𝑡𝑎𝑛𝑡
158 × 2
= g
144
= 2.194g
Actual yield = 1.6g
1.6 × 100
Percent yield = = 72.926%
2.194

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Advantages
This method of oxymethylation has provided a percentage yield of 72.926% which is
fairly high considering experimental limitations. The acid neutralized by NaOH
produces salt of sodium sulphate and water which are both neutral and thus do not cause
any further reaction with the main product or hinder with its formation. β- naphthol
methyl ether is an important intermediate in the production of naproxen, a widely used
non-steroidal anti-inflammatory agent.

Naproxen tablets
Naproxen is used to relieve pain from various
conditions such as headache, muscle aches, tendonitis,
dental pain, and menstrual cramps. It also reduces
pain, swelling, and joint stiffness caused
by arthritis, bursitis, and gout attacks.

Disadvantages
Conventionally, β-naphthol methyl ether is produced by the methylation of 2-naphthol
with dimethyl sulphate and alkali or with a methyl halide and sodium hydroxide in
tetrahydrofuran. The above methylating agents are corrosive and toxic. Moreover, these
conventional processes are atom inefficient and generate waste. For example, if one was
to alkylate 2-naphthol stoichiometrically with dimethyl sulphate and neutralize the
H2SO4with sodium carbonate, the atom efficiency would be just 0.62.

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Precautions

Avoid contact of any organic compound with skin.

Many organic compounds are toxic or carcinogenic, and so they must be

used with adequate ventilation.

β-naphthol methyl ether is an irritant and can cause irritation to eyes,

skin and other sensitive areas.

Prolonged or repeated exposure via contact may cause selective damage

of organs.

Dimethyl sulfate is carcinogenic.

Reagents used may cause genetic defects.

Make sure to use anhydrous β-naphthol.

Use clean and dry apparatus.

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 Bibliography
i. Synthesis of Nerolin by users.dickinson.edu (https://bit.ly/3JAYjDA)
ii. Vapour phase O-methylation of 2-naphthol over the solid basesalkali-loaded silica
and Cs-loaded MCM-41 by Rajaram Bal, K. Chaudhari and S. Sivasanker
(https://bit.ly/3HVVdcN)
iii. D. Barthomeuf, Catal. Rev. 38 (1996) 521.
iv. H. Hattori, Chem. Rev. 95 (1995) 537.
v. Y. Ono and T. Baba, Catal. Today 38 (1997) 321.
vi. K.R. Kloetstra, M. van Laren and H. van Bekkum, J. Chem. Soc.Faraday Trans.
93 (1997) 1211.
vii. R.A. Sheldon, Chem. Ind. (London) (6 January 1997) 13
viii. Cavrini V, Roveri P, Gatti R, Ferruzzi C, Panico AM, Pappalardo MS (1982).
"Synthesis of 2-methoxynaphthalene derivatives as potential anti-inflammatory
agents". Farmaco Sci (in Italian). 37 (3): 171–178. PMID 7067812
ix. Mann, Frederick George (1952). Practical Organic Chemistry. Longmans, Green
& Co. p. 175.
x. National Library of Medicine (https://bit.ly/3uS8gZ4)
xi. National Library of Medicine (https://bit.ly/3rW820W)
xii. National Library of Medicine (https://bit.ly/36fC8nP)

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