Hydrochloric Acid → HCID 54521383, compound

HRID 1579076Notes

Reaction equation

HRID 1579076 reaction equation
[CH3:1][C:2]([CH:7]=[CH:8][CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])=[CH:3][C:4]([OH:6])=O.[CH3:18][CH2:19]OCC.C([Li])C.Cl>C1C=CC=CC=1>[CH3:1][C:2]([CH:7]=[CH:8][CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])=[CH:3][C:4](=[O:6])[CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 4881323,7,11-Trimethyldodeca-2,4,10-trienoic acidHCID 178506846HCID 178506846, compound

Product 1

HCID 54521383HCID 54521383, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 2.4 g. of 3,7,11-trimethyldodeca-2,4,10-trienoic 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 5,9,13-trimethyltetradeca-4,6,12-trien-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-087c290f34604439bfd808aac0cf9279
Source dataset
uspto-grants-1976_02
Patent number
US03940444

Reaction notes

Loading…