Hydrochloric Acid → HCID 54500173, compound

HRID 1576588Notes

Reaction equation

HRID 1576588 reaction equation
[CH3:1][C:2]([CH:7]=[CH:8][CH2:9][CH:10]([CH3:19])[CH2:11][CH2:12][CH2:13][C:14]([CH3:18])([CH3:17])[CH2:15][CH3:16])=[CH:3][C:4]([OH:6])=O.[CH3:20][CH2:21]OCC.C([Li])C.Cl>C1C=CC=CC=1>[CH3:1][C:2]([CH:7]=[CH:8][CH2:9][CH:10]([CH3:19])[CH2:11][CH2:12][CH2:13][C:14]([CH3:18])([CH3:17])[CH2:15][CH3:16])=[CH:3][C:4](=[O:6])[CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 54353726HCID 54353726, compoundHCID 178506846HCID 178506846, compound

Product 1

HCID 54500173HCID 54500173, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 2.5 g. of 3,7,11,11-tetramethyltrideca-2,4-dienoic acid in 30 ml. of dry ether is added slowly, at 0°, 23 ml. of a one molar solution of ethyl lithium in benzene. After about three 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 5,9,13,13-tetramethylpentadeca-4,6-dien-3-one which is purified by high vacuum distillation or 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-fc87498485f34528a6a22bba822f5af6
Source dataset
uspto-grants-1976_09
Patent number
US03981922

Reaction notes

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