Water → HCID 21474500, compound

HRID 274027

Reaction equation

HRID 274027 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=2

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5850394-(Mercaptomethyl)benzoic acidHCID 27954665,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl chloride

Product 1

HCID 21474500HCID 21474500, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

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

  1. extractionthe mixture is extracted with ethyl ether
  2. customthe organic phase is separated after settling
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue obtained
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-828056ae12e341198463f0990e65d56d
Source dataset
uspto-grants-1995_02
Patent number
US05387594

Linked notes

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