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ChemicalBook CAS DataBase List 2,2-Dimethyl-2,3-dihydrobenzofuran-4-carboxylic acid
123656-35-9

2,2-Dimethyl-2,3-dihydrobenzofuran-4-carboxylic acid synthesis

7synthesis methods
4-Benzofurancarboxylic acid, 2,3-dihydro-2,2-dimethyl-, ethyl ester

209256-58-6

2,2-Dimethyl-2,3-dihydrobenzofuran-4-carboxylic acid

123656-35-9

Ethyl 2,2-dimethyl-2,3-dihydrobenzofuran-4-carboxylate (10 g, 45 mmol) was used as starting material, which was mixed with a solution of sodium hydroxide (16.3 ml, 10N, 163 mmol) in ethanol (50 ml) and heated to reflux for 2 hours. Upon completion of the reaction, the mixture was concentrated under vacuum and subsequently diluted with water and acidified with 12N hydrochloric acid to the appropriate pH. The precipitate produced after acidification was collected by filtration and dried in air to give 2,2-dimethyl-2,3-dihydrobenzofuran-4-carboxylic acid (8.6 g, 100% yield).

4-Benzofurancarboxylic acid, 2,3-dihydro-2,2-dimethyl-, ethyl ester

209256-58-6
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2,2-Dimethyl-2,3-dihydrobenzofuran-4-carboxylic acid

123656-35-9
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Yield:123656-35-9 100%

Reaction Conditions:

Stage #1: ethyl 2,2-dimethyl-2,3-dihydro-benzofuran-4-carboxylatewith sodium hydroxide in ethanol; for 2 h;Heating / reflux;
Stage #2: with hydrogenchloride in water;

Steps:

6.3

Ethyl 2,2-dimethyl-2,3-dihydro-benzofuran-4-carboxylic acid (10 g, 45 mmol) was heated to reflux with sodium hydroxide (16.3 ml of 10 N, 163 mmol) in ethanol (50 ml) for 2 hr. The mixture was concentrated in vacuo, diluted with water and made acidic with 12 N HCl. The precipitate was filtered and air dried (8.6 g, 100%).

References:

EP1027043,2004,B1 Location in patent:Page/Page column 20