3,7,11-Trimethyldodeca-1,6,10-trien-3-ol → 5,9,13-Pentadecatrien-2-one, 6,10,14-trimethyl-

HRID 2225465Notes

Reaction equation

HRID 2225465 reaction equation
O[C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH3:10])([CH:4]=[CH2:5])[CH3:3].C([O-])(=O)[CH2:18][C:19]([CH3:21])=[O:20]>>[CH3:3][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:10])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])=[CH:4][CH2:5][CH2:18][C:19](=[O:20])[CH3:21]

Participants

3

Reactant 2

HCID 88883,7,11-Trimethyldodeca-1,6,10-trien-3-olHCID 6971017Acetoacetate

Product 1

HCID 612065,9,13-Pentadecatrien-2-one, 6,10,14-trimethyl-

Procedure

Nerolidol [compound (5) (manufactured by Takasago International Corporation] to be used as a starting material was subjected to Carroll reaction using acetoacetate in accordance with the method of W. Kimel et al. [J. Org. Chem., 23(2), pp. 153-157 (1958)] to give 6,10,14-trimethyl-5,9,13-pentadecatrien-2-one [compound (6)].

Workup

  1. customwas subjected to Carroll reaction

Sources & evidence

ORD record
ord-93f0dd2f716d436f9d9f3420594db690
Source dataset
uspto-grants-1994_09
Patent number
US05344850

Reaction notes

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