Methyl 4-(N-methyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylacetamido)benzoate → 4-(N-Methyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylacetamido)benzoic acid
Reaction equation
[CH3:1][N:2]([C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=1)[C:3](=[O:19])[CH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:11]([CH3:16])([CH3:15])[CH2:10][CH2:9][C:8]([CH3:18])([CH3:17])[C:7]=2[CH:6]=1>[OH-].[Na+]>[CH3:1][N:2]([C:20]1[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1)[C:3](=[O:19])[CH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:11]([CH3:15])([CH3:16])[CH2:10][CH2:9][C:8]([CH3:18])([CH3:17])[C:7]=2[CH:6]=1Participants
3
Procedure
1.8 g (4.6 mmol) of the ester obtained above in (a), 100 ml of 2N methanolic sodium hydroxide and 50 ml of TMF are introduced into a round-bottomed flask. The mixture is stirred at room temperature for one hour and evaporated to dryness, the residue is taken up with water, the mixture is extracted with ethyl ether and the aqueous phase is separated after settling has taken place. The aqueous phase is acidified to pH 1 with concentrated hydrochloric acid and extracted with ethyl ether and the organic phase is separated after settling has taken place, dried over magnesium sulphate and evaporated. 1.6 g (94%) of the expected acid, having a melting point of 192°-193° C., are collected.
Workup
- additionare introduced into a round-bottomed flask
- customevaporated to dryness
- extractionthe mixture is extracted with ethyl ether
- customthe aqueous phase is separated after settling
- extractionextracted with ethyl ether
- customthe organic phase is separated after settling
- dry with materialdried over magnesium sulphate
- customevaporated
- customare collected
Sources & evidence
- ORD record
- ord-96d3ec50187748efb98b7a9374237b8f
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05688817
Reaction notes
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