Benzene → Isopropyl 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoate

HRID 1605135Notes

Reaction equation

HRID 1605135 reaction equation
[CH3:1][S:2][C:3]([CH3:19])([CH3:18])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:17])[CH2:8][CH:9]=[CH:10][C:11]([CH3:16])=[CH:12][C:13]([OH:15])=[O:14].[CH:20]1[CH:25]=CC=C[CH:21]=1.C(Cl)(=O)C(Cl)=O.C(=O)(O)[O-].[Na+]>CCOCC.C(O)(C)C>[CH3:1][S:2][C:3]([CH3:18])([CH3:19])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:17])[CH2:8][CH:9]=[CH:10][C:11]([CH3:16])=[CH:12][C:13]([O:15][CH:20]([CH3:25])[CH3:21])=[O:14]

Participants

7

Reactant 4

HCID 241BenzeneHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 5422430711-Methylthio-3,7,11-trimethyldodeca-2,4-dienoic acid

Product 1

HCID 54300429Isopropyl 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

To 0.6 g. of 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoic acid in 10 ml. of dry benzene is added 0.23 ml. of oxalyl chloride at room temperature with stirring. After 2 hours, isopropanol (2ml.) is added and the mixture allowed to stand at room temperature for about 2 hours. Ether and saturated sodium bicarbonate is added and the organic phase separated. The organic phase is washed with aqueous sodium bicarbonate, saturated sodium chloride, dried over calcium sulfate and evaporated to yield isopropyl 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoate.

Workup

  1. waitto stand at room temperature for about 2 hours
  2. customthe organic phase separated
  3. washThe organic phase is washed with aqueous sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried over calcium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-2275bdf051b343de9dcf80ef654d801d
Source dataset
uspto-grants-1976_04
Patent number
US03948996

Reaction notes

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