Bromoethene → Nerolidol

HRID 436884Notes

Reaction equation

HRID 436884 reaction equation
[CH3:1][C:2]([CH3:14])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:13])=[CH:7]/[CH2:8][CH2:9][C:10]([CH3:12])=[O:11].[Mg].[CH:16](Br)=[CH2:17]>O1CCCC1>[CH3:1][C:2]([CH3:14])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:13])=[CH:7]/[CH2:8][CH2:9][C:10]([OH:11])([CH:16]=[CH2:17])[CH3:12]

Participants

5

Reactant 3

HCID 11641BromoetheneHCID 1549778GeranylacetoneHCID 5462224Magnesium

Product 1

HCID 5284507Nerolidol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to the method reported by A. Ofner et al. in Helv. Chim. Acta., 42 2577- 2584 (1959), cis- or trans-nerolidol was prepared respectively from cis- or trans-geranylacetone. That is, in 420 ml of tetrahydrofuran was placed 12.5 g of freshly-prepared metallic magnesium turnings and 60 g of vinyl bromide was added dropwise thereto under water cooling to form a Grignard reagent. 50 g cis- or trans-geranylacetone was added dropwise thereto at 25° C. The reaction mixture was neutralized with ammonium chloride and extracted with ether. The extract was dried over sodium sulfate and distilled off under reduced pressure. The residue was subjected to vacuum distillation to give cis-nerolidol from cis-geranylacetone in a yield of 82%. The product was identified by the standard product obtained in Example 12.

Workup

  1. additionwas added dropwise

Sources & evidence

ORD record
ord-71632d25062341f0966dee5286df72d0
Source dataset
uspto-grants-1977_06
Patent number
US04028385

Reaction notes

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