Allyl Alcohol → 14-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal

HRID 486864Notes

Reaction equation

HRID 486864 reaction equation
C(O)C=C.[Cl:5][CH2:6][C:7]([CH3:26])=[CH:8][CH2:9][CH2:10][C:11]([CH3:25])=[CH:12][CH2:13][CH2:14][C:15]([CH3:24])=[CH:16][CH:17]=[C:18]([CH:21]([CH3:23])[CH3:22])[CH2:19][OH:20].[Mn]([O-])([O-])(=O)=O.[Ba+2]>C(Cl)Cl>[Cl:5][CH2:6][C:7]([CH3:26])=[CH:8][CH2:9][CH2:10][C:11]([CH3:25])=[CH:12][CH2:13][CH2:14][C:15]([CH3:24])=[CH:16][CH:17]=[C:18]([CH:21]([CH3:22])[CH3:23])[CH:19]=[O:20]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 3084030Barium manganateHCID 5368470314-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraen-1-ol

Product 1

HCID 5388146714-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenalYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the allylalcohol which is 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraen-1-ol (492 mg, 1.51 mmol) in methylene chloride (22 ml) is added powdered barium manganate (8.5 g) and the mixture is vigorously stirred under argon atmosphere. After 8 hours, disappearance of the starting compound is confirmed and the reaction mixture is filtered and washed. The filtrate and the washing liquid are combined and concentrated. The resulting residue is purified by silica gel column chromatography (n-nexane/ethyl acetate=15:1) to give the desired 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal (468 mg, 95%).

Workup

  1. filtrationthe reaction mixture is filtered
  2. washwashed
  3. concentrationconcentrated
  4. customThe resulting residue is purified by silica gel column chromatography (n-nexane/ethyl acetate=15:1)

Sources & evidence

ORD record
ord-17e3dc326e68418998b35e2f3b930b64
Source dataset
uspto-grants-1994_03
Patent number
US05292911

Reaction notes

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