Hydrochloric Acid → 10-Methoxy-6,10-dimethyl-5-undecene-2-one

HRID 436878Notes

Reaction equation

HRID 436878 reaction equation
C1CO[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:17])[CH2:9][CH2:10][CH2:11][C:12]([O:15][CH3:16])([CH3:14])[CH3:13])([CH3:4])[O:2]1.Cl>CO.O>[CH3:16][O:15][C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][CH2:9][C:8]([CH3:17])=[CH:7][CH2:6][CH2:5][C:3](=[O:2])[CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 77886384HCID 77886384, compound

Product 1

HCID 5396652510-Methoxy-6,10-dimethyl-5-undecene-2-oneYield 97.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

This and the next reaction could be effected with the E and Z isomers or mixtures thereof. A solution of 1.1 g of 2,2-ethylenedioxy-10-methoxy-6,10-dimethyl-5-undecene in 22 ml of methanol containing 11 ml of 0.5N aqueous hydrochloric acid was stirred for 20 hours at room temperature and was then diluted with water and extracted with petroleum ether (b.p.= 40°-75° C.). The extracts were washed with an aqueous sodium bicarbonate solution, then with water and evaporated to dryness to obtain 900 mg of 10-methoxy-6,10-dimethyl-5-undecene-2-one in the form of a colorless oil which was used as is for the next step.

Workup

  1. customThis and the next reaction
  2. extractionextracted with petroleum ether (b.p.= 40°-75° C.)
  3. washThe extracts were washed with an aqueous sodium bicarbonate solution
  4. customwith water and evaporated to dryness

Sources & evidence

ORD record
ord-ffc1eb2e07c54bd5b522fd7ebf07e5e6
Source dataset
uspto-grants-1977_06
Patent number
US04028386

Reaction notes

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