Hexadeca-7,11-dien-1-yl acetate → 11-Hexadecen-7-yn-1-ol, 1-acetate, (11E)-

HRID 1973170Notes

Reaction equation

HRID 1973170 reaction equation
C(Br)CCCCCO.[C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH:20][CH2:21][CH2:22][CH:23]=[CH:24][CH2:25][CH2:26][CH2:27][CH3:28])(=[O:11])[CH3:10]>C1COCC1>[C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]#[C:20][CH2:21][CH2:22]/[CH:23]=[CH:24]/[CH2:25][CH2:26][CH2:27][CH3:28])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 39848Hexadeca-7,11-dien-1-yl acetateHCID 779706-Bromo-1-hexanol

Product 1

HCID 643704211-Hexadecen-7-yn-1-ol, 1-acetate, (11E)-Yield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The THP derivative of hexamethylene bromohydrin in THF is added and the reaction mixture is worked up as described for 7,11-hexadecadienyl acetate. Vacuum distillation of the residue affords (E)-11-hexadecen-7-ynyl acetate, bp 134°-136°/1 mm, nD21 1.4655, in about 55-60% yield, contaminated with 0-5% of 7,11-hexadecadiynyl acetate.

Workup

  1. distillationVacuum distillation of the residue

Sources & evidence

ORD record
ord-2da60ee27f6943d087db3517e1739c2e
Source dataset
uspto-grants-1976_12
Patent number
US03996270

Reaction notes

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