Water → 3,3-Dimethyl-2,3-dihydro-1-benzofuran-5-ol
Reaction equation
C(S)C.[H-].[Na+].C[O:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]=2[CH:18]=1.O>CN(C)C=O>[CH3:16][C:13]1([CH3:17])[C:12]2[CH:18]=[C:8]([OH:7])[CH:9]=[CH:10][C:11]=2[O:15][CH2:14]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of ethanethiol (12.6 parts) in dimethyl formamide (60 parts) was added with stirring under nitrogen over a period of 20 minutes to a mixture of sodium hydride (6.6 parts of 80% dispersion in oil) and dry dimethyl formamide (60 parts) cooled to 0° C. After 10 minutes, a solution of 2,3-dihydro-5-methoxy-3,3-dimethylbenzofuran (18 parts) in dimethyl formamide (40 parts) was added and the mixture boiled under reflux in a nitrogen atmosphere for 3 hours. The mixture was then added to water and the aqueous phase washed with chloroform, acidified with hydrochloric acid and extracted into ether. The ether was evaporated off to yield 2,3-dihydro-3,3-dimethyl-benzofuran-5-ol (5.4 parts) as a brown oil.
Workup
- temperatureunder reflux in a nitrogen atmosphere for 3 hours
- washthe aqueous phase washed with chloroform
- extractionextracted into ether
- customThe ether was evaporated off
Sources & evidence
- ORD record
- ord-e49145092cdf4b1ca864bdd569e42458
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04222767
Reaction notes
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