Water → 4-[2-[[1,1'-Biphenyl]-2-yl]-2-oxoethoxy]-alpha-oxobenzeneacetic acid
Reaction equation
C[O:2][C:3](=[O:28])[C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:14])=[CH:7][CH:6]=1.[OH-].[Na+].O>CO>[C:16]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:13](=[O:14])[CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:4](=[O:27])[C:3]([OH:28])=[O:2])=[CH:6][CH:7]=1Participants
Procedure
A solution of 4-[-2-[[1,1'-biphenyl]-2-yl]-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester (0.563 g) in warm methanol (5 mL) was treated with 1N sodium hydroxide (3.3 mL). Within 5 minutes water (30 mL) was added, then after the methanol was removed in vacuo, the mixture was acidified with 1N hydrochloric acid (4.1 mL) and extracted with dichloromethane (1×60 mL, 2×10 mL). The combined organic layers were washed with water, then dried (MgSO4) and evaporated. The resulting yellow foam was taken up in diethyl ether, and after the the mixture was filtered to remove some insoluble material, the fillrate was evaporated and the residue was lyophilized from benzene to furnish 0.36 g of 4-[2-[[1,1'-biphenyl]-2-yl]-2-oxoethoxy]-alpha-oxobenzeneacetic acid.
Workup
- customafter the methanol was removed in vacuo
- extractionextracted with dichloromethane (1×60 mL, 2×10 mL)
- washThe combined organic layers were washed with water
- dry with materialdried (MgSO4)
- customevaporated
- filtrationafter the the mixture was filtered
- customto remove some insoluble material
- customthe fillrate was evaporated
Sources & evidence
- ORD record
- ord-c75670e30abd40af91c3de1f0471ec3f
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05344843
Reaction notes
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