Ammonium Chloride → HCID 53818560, compound

HRID 1579080Notes

Reaction equation

HRID 1579080 reaction equation
[OH:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:16])[CH2:7][CH:8]=[CH:9][C:10]([CH3:15])=[CH:11][C:12]([OH:14])=O.[CH2:19]([Li])[CH3:20].[Cl-].[NH4+]>C1C=CC=CC=1.CCOCC>[OH:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:16])[CH2:7][CH:8]=[CH:9][C:10]([CH3:15])=[CH:11][C:12](=[O:14])[CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 5379374211-Hydroxy-3,7,11-trimethyldodeca-2,4-dienoic acidHCID 178506846HCID 178506846, compound

Product 1

HCID 53818560HCID 53818560, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 3.35 g. of 11-hydroxy-3,7,11-trimethyldodeca-2,4-dienoic acid in 50 ml. ether at -20°C under nitrogen is added dropwise 59.1 ml. of a 0.67 molar solution of ethyllithium in benzene. The reaction mixture is allowed to warm to room temperature and is stirred overnight. The reaction mixture is then taken up in a mixture of ether and saturated aqueous ammonium chloride. The organic layer is separated, is washed with saturated aqueous ammonium chloride, 5% aqueous sodium bicarbonate, water, and saturated sodium chloride, is dried over calcium sulfate, and the solvent is removed to yield 13-hydroxy-5,9,13-trimethyltetradeca-4,6-dien-3-one which is purified by preparative thin layer chromatography (50% ether/hexane).

Workup

  1. customThe organic layer is separated
  2. washis washed with saturated aqueous ammonium chloride, 5% aqueous sodium bicarbonate, water, and saturated sodium chloride
  3. dry with materialis dried over calcium sulfate
  4. customthe solvent is removed

Sources & evidence

ORD record
ord-5ca2bfd760604791b75a8f0a2ead98b8
Source dataset
uspto-grants-1976_02
Patent number
US03940444

Reaction notes

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