Synthesis of (ethoxymethyl)benzene

Preparation of (ethoxymethyl)benzene

Alternative Names: Benzyl ethyl ether; Benzene, (ethoxymethyl)-; Ether, benzyl ethyl; Ethoxymethylbenzene;

Preparation of (ethoxymethyl)benzene

Preparation of (ethoxymethyl)benzene

In a round bottom flask a mixture of 4 g of potassium hydroxide dissolved in 200 ml of water and 25 ml ethanol are placed. The flask is fitted with a reflux condenser and gently heated until the potassium hydroxide fully dissolves (small amount of potassium hydroxide may remain undissolved). The solution is cooled and 5.8 ml of benzyl chloride are added. Then the mixture is gently heated to the boiling point, turbulent reaction takes place which last approximately 15 minutes. At the end of the reaction the flask is placed in a hot water bath and heated for another 20 min. When the reaction is complete the mixture is cooled in a cold water bath, mixed with 50 ml of ice-water and shaken until all solids dissolve. Small portions of 2N hydrochloric acid are added until the aqueous layer is acidic to litmus. The resulting ester is separated and washed with water (2 x 5 mL), dried over calcium chloride, filtered  and distilled, collecting the fraction with boiling at 180-187° C. The yield of (ethoxymethyl)benzene is about 4 g (60% of theory); nD=1, 4955 at 20° C.

Лабораторные работы в органическом практикуме, А.Е., Агрономов, 63, 1974 (Laboratory work in the organic practice, AE, Agronomov 63, 1974)

IUPAC Name

ethoxymethylbenzene

InChI

InChI=1S/C9H12O/c1-2-10-8-9-6-4-3-5-7-9/h3-7H,2,8H2,1H3

InChI Key

AXPZDYVDTMMLNB-UHFFFAOYSA-N

Canonical SMILES

CCOCC1=CC=CC=C1

Depositor-Supplied Synonyms

(Ethoxymethyl)benzene, Benzyl ethyl ether, 539-30-0, Benzene, (ethoxymethyl)-, Ether, benzyl ethyl, Ethoxymethylbenzene, Benzyl ethyl oxide, Ethyl benzyl ether, Benzylethylether, Benzene, ethoxymethyl-, UNII-5Y0D90XR7K, ethoxyphenylmethane, AXPZDYVDTMMLNB-UHFFFAOYSA-N, SBB061196, 118402-27-0, ACMC-20dpkg, (Ethoxymethyl)benzene #, AC1LAZG7, AC1L1W4T, SCHEMBL16478, Ether, benzyl ethyl (8CI), METHYL, ETHOXYPHENYL-, ARONIS24216, FEMA No. 2144, 5Y0D90XR7K, AC1Q386M, CTK0F9886, NSC8066, MolPort-001-788-460, NSC 8066, NSC-8066, EINECS 208-714-6, ZINC01586382, AKOS005267098, MCULE-6632710098, AJ-27557, AK113539, AN-21317, CJ-25246, OR023073, OR225737, OR280949, S562, AI3-02270, DB-052428, KB-209325, ST2402533, TR-019052, 4CH-017431, FT-0622150, FT-0622819, ST51047246, Z-0824, I01-7534, 3B3-051872, InChI=1/C9H12O/c1-2-10-8-9-6-4-3-5-7-9/h3-7H,2,8H2,1H

Removed Synonyms

CID10873

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