Methyl bromoacetate → Oleyl bromoacetate

HRID 82436

Reaction equation

[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Br:20][CH2:21][C:22](OC)=[O:23]>>[Br:20][CH2:21][C:22]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:23]

Participants

Reactant 2

HCID 60984Methyl bromoacetate

HCID 5284499Oleyl Alcohol

Product 1

HCID 56640678Oleyl bromoacetate

Procedure

Technical grade oleyl alcohol (85 wt %; 10 g; 37.2 mmol) was combined with Novozym 435 (200 mg) in an amber bottle. Methyl bromoacetate (6.84 g; 44.7 mmol; 1.2 equiv.) was added, and the mixture was sealed and stirred at room temperature overnight to afford about 50% conversion to oleyl bromoacetate. The mixture was then purged with a subsurface stream of nitrogen 2.5 days to afford 98.5% conversion of oleyl alcohol to oleyl bromoacetate according to GC analysis. The mixture was filtered, and the solid was washed with toluene. The filtrate was concentrated to give the desired product as a viscous colorless oil (13.19 g, 91%). The product was used in the subsequent reactions without further purification.

Workup

customthe mixture was sealed

Sources & evidence

ORD record: ord-7b981f4a1b054da2a604a68cfd4aad30
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846723B2

Linked notes

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