Hydrochloric Acid → Isobutoxyacryloyl chloride

HRID 1937057Notes

Reaction equation

[CH:1]([O:3][CH2:4][CH:5]([CH3:7])[CH3:6])=[CH2:2].[C:8](Cl)([Cl:10])=[O:9].Cl>>[CH2:4]([O:3][CH:1]=[CH:2][C:8]([Cl:10])=[O:9])[CH:5]([CH3:7])[CH3:6]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 6371Phosgene

HCID 7992Vinyl isobutyl ether2×

Product 1

HCID 57093342Isobutoxyacryloyl chloride

Conditions

Temperature: 52.5 °C

Procedure

100 g (1 mol) of isobutyl vinyl ether are initially charged in a 2 1 stirred apparatus and heated to 50-55° C. 1024 g (10.4 mol) of phosgene are subsequently introduced over a period of 21 h, and 900 g (9 mol) of isobutyl vinyl ether are added dropwise over a period of 19 h. After an extra reaction time of 0.5 hours, the reaction mixture is heated to 80° C. with nitrogen stripping to eliminate hydrogen chloride. The low-boilers are then distilled off via a 15 cm Vigreux column, and the residue is analyzed by gas chromatography. This gives 1551 g (80%) of crude isobutoxyacrylolyl chloride (calc. 100%).

Workup

temperatureAfter an extra reaction time of 0.5 hours, the reaction mixture is heated to 80° C. with nitrogen stripping
distillationThe low-boilers are then distilled off via a 15 cm Vigreux column

Sources & evidence

ORD record: ord-de50ebf5d374497598d02513fb27b779
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06392058B1

Reaction notes

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