Water → 4-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthoylthiomethyl)benzoic acid
Reaction equation
[SH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:19][C:20]1([CH3:35])[CH2:29][CH2:28][C:27]([CH3:31])([CH3:30])[C:26]2[CH:25]=[C:24]([C:32](Cl)=[O:33])[CH:23]=[CH:22][C:21]1=2.O>C1COCC1.CCCCCC.C(OCC)C>[CH3:19][C:20]1([CH3:35])[CH2:29][CH2:28][C:27]([CH3:30])([CH3:31])[C:26]2[CH:25]=[C:24]([C:32]([S:1][CH2:2][C:3]3[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=3)=[O:33])[CH:23]=[CH:22][C:21]1=2Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
1.68 g (10 mmol) of 4-mercaptomethylbenzoic acid, 2.8 ml (20 mmol) of triethylamine and 50 ml of THF are introduced into a round-bottomed flask. A solution of 2.5 g (10 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl -2-naphthoyl chloride in 50 ml of THF is added dropwise and the mixture is stirred at room temperature for four hours. The reaction medium is poured into water, the mixture is extracted with ethyl ether and the organic phase is separated after settling has taken place, then dried over magnesium sulphate and evaporated. The residue obtained is ground in 50 ml of a mixture of ethyl ether and hexane (50:50) and then filtered off. 2.5 g (66%) of the expected acid, melting point 150-151° C, are obtained.
Workup
- extractionthe mixture is extracted with ethyl ether
- customthe organic phase is separated after settling
- dry with materialdried over magnesium sulphate
- customevaporated
- customThe residue obtained
- filtrationfiltered off
Sources & evidence
- ORD record
- ord-838284871af145ee892a2f4c19e1da2f
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05439925
Reaction notes
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