Sulfuric Acid → 90103-48-3

HRID 1194790

Reaction equation

HRID 1194790 reaction equation
[CH3:1][C:2]1([CH3:27])[C:10]2[CH:9]=[C:8]([C:11]([CH3:24])=[CH:12][C:13]3[CH:23]=[CH:22][C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][CH:14]=3)[S:7][C:6]=2[C:5]([CH3:26])([CH3:25])[CH2:4][CH2:3]1.[OH-].[K+].S(=O)(=O)(O)O>C(O)C.O>[CH3:1][C:2]1([CH3:27])[C:10]2[CH:9]=[C:8](/[C:11](/[CH3:24])=[CH:12]/[C:13]3[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:22][CH:23]=3)[S:7][C:6]=2[C:5]([CH3:26])([CH3:25])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 53678243Ethyl p-[2-(4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thien-2-yl)propenyl]-benzoate

Product 1

HCID 643976390103-48-3Yield 86.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

3.0 g of ethyl p-[2-(4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thien-2-yl)propenyl]benzoate are dissolved in 100 ml of ethanol and the solution is treated with a solution of 3.9 g of potassium hydroxide in 20 ml of water. After stirring at 50° C. for 3 hours, the mixture is cooled, poured into ice-water and acidified with 2N sulphuric acid. The mixture is extracted with ethyl acetate, the organic phase is washed with water, dried over sodium sulphate and evaporated. After recrystallization of the residue from ethyl acetate, there are obtained 2.4 g of p-[(E)-2-(4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thien-2-yl)propenyl]benzoic acid in the form of pale yellowish crystals, m.p. 236°-238° C.

Workup

  1. temperaturethe mixture is cooled
  2. extractionThe mixture is extracted with ethyl acetate
  3. washthe organic phase is washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customAfter recrystallization of the residue from ethyl acetate, there

Sources & evidence

ORD record
ord-b4b1a2a088214634af74ec2d4337981c
Source dataset
uspto-grants-1989_03
Patent number
US04816476

Linked notes

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