Ethanol → ethyl 3,4-dihydro-6-hydroxy-2H-1-benzopyran-2-carboxylate
Reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]([OH:13])=[O:12])[CH2:8][CH2:7][C:6]=2[CH:14]=1.S(=O)(=O)(O)O.[CH2:20](O)[CH3:21]>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]([O:13][CH2:20][CH3:21])=[O:12])[CH2:8][CH2:7][C:6]=2[CH:14]=1Participants
Procedure
A mixture of 60 parts of 3,4-dihydro-6-hydroxy-2H-1-benzopyran-2-carboxylic acid, 800 parts of ethanol and 5.52 parts of concentrate sulfuric acid was stirred for 3 hours at reflux temperature. The reaction mixture was evaporated. Water was added and the product was extracted with trichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was solidified in petroleumether. The product was filtered off and dried, yielding 48 parts (70%) of ethyl 3,4-dihydro-6-hydroxy-2H-1-benzopyran-2-carboxylate as a residue (intermediate 21).
Workup
- temperatureat reflux temperature
- customThe reaction mixture was evaporated
- additionWater was added
- extractionthe product was extracted with trichloromethane
- washThe extract was washed with water
- customdried
- filtrationfiltered
- customevaporated
- customThe residue was purified by column chromatography over silica gel using
- additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
- customThe pure fractions were collected
- customthe eluent was evaporated
- filtrationThe product was filtered off
- customdried
Sources & evidence
- ORD record
- ord-772754508fcd4df3b65a89c0d1d095d7
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04654362
Reaction notes
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