HCID 23049242, compound → (3,3,6,6-Tetramethylcyclohex-1-en-1-yl)acetic acid

HRID 542907Notes

Reaction equation

HRID 542907 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[C:4]([CH:10](S(C2C=CC=CC=2)(=O)=O)[C:11]([OH:13])=[O:12])=[CH:3]1>C(O)C.[Na].[Hg]>[CH3:1][C:2]1([CH3:23])[CH2:7][CH2:6][C:5]([CH3:8])([CH3:9])[C:4]([CH2:10][C:11]([OH:13])=[O:12])=[CH:3]1

Participants

4

Reactant 1

HCID 23049242HCID 23049242, compound

Product 1

HCID 23049232(3,3,6,6-Tetramethylcyclohex-1-en-1-yl)acetic acidYield 84.9%

Reagents, catalysts & solvents 2

HCID 9837419Sodium amalgamCatalystHCID 702EthanolSolvent

Procedure

20.6 g of 3,3,6,6-tetramethyl-α-(phenylsulphonyl)-1-cyclohexen-1-acetic acid are dissolved in 800 ml of ethanol and the solution is treated at 0° C. with 107.1 g of sodium amalgam (5%). The mixture is stirred at room temperature for 4.5 hours, the solution is decanted off from the mercury, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with water, dried, evaporated and filtered over silica gel (eluting agent hexane/ether 1:1). After recrystallization from hexane, there are obtained 10.2 g of 3,3,6,6-tetramethyl-1-cyclohexen-1-acetic acid in the form of colorless crystals, m.p. 50°-54° C.

Workup

  1. customthe solution is decanted off from the mercury
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. customdried
  5. customevaporated
  6. filtrationfiltered over silica gel (eluting agent hexane/ether 1:1)
  7. customAfter recrystallization from hexane, there

Sources & evidence

ORD record
ord-7843cf9780f14d5ca4112d4d94e142cf
Source dataset
uspto-grants-1987_04
Patent number
US04659735

Reaction notes

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