Hydrochloric Acid → 13-Methylthio-5,9,13-trimethyltetradeca-4,6-dien-3-one

HRID 1605136Notes

Reaction equation

HRID 1605136 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.[CH3:20][CH2:21]OCC.C([Li])C.Cl>C1C=CC=CC=1>[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](=[O:15])[CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 5422430711-Methylthio-3,7,11-trimethyldodeca-2,4-dienoic acidHCID 178506846HCID 178506846, compound

Product 1

HCID 5443428813-Methylthio-5,9,13-trimethyltetradeca-4,6-dien-3-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 2.5 g. of 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoic acid in 20 ml. of dry ether is added slowly at 0°, 23 ml. of a one molar solution of ethyl lithium in benzene. After about 3 hours at 20°, the mixture is poured into iced 1N hydrochloric acid (100 ml.) with vigorous stirring. The ether layer is separated, combined with ethereal washings of the aqueous phase, washed with water, saturated potassium bicarbonate and then saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to yield 13-methylthio-5,9,13-trimethyltetradeca-4,6-dien-3-one, which can be purified by chromatography.

Workup

  1. customThe ether layer is separated
  2. washwashed with water, saturated potassium bicarbonate
  3. dry with materialsaturated brine, dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-551fe349d4b34aaab23a3192045b1cc8
Source dataset
uspto-grants-1976_04
Patent number
US03948996

Reaction notes

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