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

HRID 1886199Notes

Reaction equation

HRID 1886199 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 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The allyl alcohol compound shown above [14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraen-1-ol] (492 mg, 1.51 mmol) obtained in Reference Example 1 was dissolved in methylene chloride (22 ml). To the solution was added powdery barium manganate (8.5 g), and the resultant mixture was stirred under argon atmosphere. Disappearance of the starting material was confirmed eight hours later, and the mixture was filtered and washed. The filtrate and washings were combined and concentrated. The residue was chromatographed on a silica gel column (Eluent:n-hexane:ethyl acetate=15:1) to give the objective 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal (468 mg, 95%).

Workup

  1. customobtained in Reference Example 1
  2. filtrationlater, and the mixture was filtered
  3. washwashed
  4. concentrationconcentrated
  5. customThe residue was chromatographed on a silica gel column (Eluent:n-hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-cf2b4f5f6a74485997f8c057e4cc32a5
Source dataset
uspto-grants-1992_09
Patent number
US05149843

Reaction notes

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