11-Bromoundecanoic acid → Undecanoyl chloride, 11-bromo-

HRID 434479

Reaction equation

[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O.S(Cl)([Cl:17])=O>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([Cl:17])=[O:14]

Participants

Reactant 2

HCID 1781211-Bromoundecanoic acid

HCID 24386Thionyl Chloride

Product 1

HCID 85202Undecanoyl chloride, 11-bromo-Yield 90%

Procedure

55 g (0.20 moles) of recrystallised 11-bromo undecanoic acid were refluxed with 48 g (0.4 moles) of thionyl chloride for 3 hours. Excess thionyl chloride was then removed by vacuum distillation at 10-14 mm Hg pressure. The crude acid chloride remaining was distilled under higher vacuum (0.1 mm Hg) to give 50 g (0.18 moles) of pure 11-bromo undecanoyl chloride.

Workup

customExcess thionyl chloride was then removed by vacuum distillation at 10-14 mm Hg pressure
distillationThe crude acid chloride remaining was distilled under higher vacuum (0.1 mm Hg)

Sources & evidence

ORD record: ord-a298f05a422243b997ac9596b1f1506d
Source dataset: uspto-grants-1983_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04397757

Linked notes

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