Methanol → Methyl 11-methoxy-7,11-dimethyl-3-oxo-6-dodecenoate

HRID 436880Notes

Reaction equation

HRID 436880 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]([CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[CH:8][CH2:9][CH2:10][C:11](=[O:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14].[CH3:24][OH:25]>O>[CH3:24][O:25][C:21]([CH3:23])([CH3:22])[CH2:20][CH2:19][CH2:18][C:7]([CH3:6])=[CH:8][CH2:9][CH2:10][C:11](=[O:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 53708905HCID 53708905, compound

Product 1

HCID 54124623Methyl 11-methoxy-7,11-dimethyl-3-oxo-6-dodecenoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product can be obtained in the form of a mixture of E and Z isomers by adding dropwise 3 ml of concentrated sulfuric acid to a solution of 7.6 g of the product of Example 3 in 45 ml of methanol and stirring the mixture at room temperature for 40 hours. The mixture was diluted with water and extracted with methylene chloride. The extracts were washed with water, dried over sodium sulfate and evaporated to dryness and the residue was chromatographed over silica and was eluted with a 9-1 benzene-ethyl acetate mixture to obtain 1.3 g of methyl 11-methoxy-7,11-dimethyl-3-oxo-6-dodecenoate in the form of a colorless oil.

Workup

  1. customThe product can be obtained in the form of a mixture of E and Z isomers
  2. extractionextracted with methylene chloride
  3. washThe extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customthe residue was chromatographed over silica
  7. washwas eluted with a 9-1 benzene-ethyl acetate mixture

Sources & evidence

ORD record
ord-d35d695c5bf94e7da610d4125c65cffd
Source dataset
uspto-grants-1977_06
Patent number
US04028386

Reaction notes

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