Sodium Hydroxide → 4-[2-(2-Naphthalenyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid
Reaction equation
C[O:2][C:3](=[O:26])[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[O:14])=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O1CCCC1>[CH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[C:13](=[O:14])[CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:4](=[O:25])[C:3]([OH:26])=[O:2])=[CH:6][CH:7]=1Participants
5
Procedure
A solution of 4-[2-(2-naphthalenyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester (0.57 g) in methanol (3 mL) and tetrahydrofuran (8 mL) was treated with 1N sodium hydroxide (1.7 mL) and a white precipitate formed after 1 minutes. After 5 minutes, the reaction mixture was concentrated, the residue was acidified with excess hydrochloric acid and partitioned between dichloromethane (100 mL) and water (10 mL). The organic layer was dried (MgSO4) and concentrated. The resulting residue was crystallized from ethyl acetate-hexane-tetrahydrofuran to give 0.343 of 4-[2-(2-naphthalenyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid, mp 167°-170° C.
Workup
- customa white precipitate formed after 1 minutes
- concentrationthe reaction mixture was concentrated
- custompartitioned between dichloromethane (100 mL) and water (10 mL)
- dry with materialThe organic layer was dried (MgSO4)
- concentrationconcentrated
- customThe resulting residue was crystallized from ethyl acetate-hexane-tetrahydrofuran
Sources & evidence
- ORD record
- ord-d3817319b380455fabb39ce408a7c76e
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05344843
Reaction notes
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