Water → HCID 15078144, compound

HRID 263310Notes

Reaction equation

HRID 263310 reaction equation
[CH2:1](Cl)[CH:2]=[CH2:3].O.[C:6]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:7]O.[Na].[OH-].[Na+].[CH3:16][CH2:17][O:18][CH2:19][CH2:20][OH:21]>>[CH2:17]([O:18][CH2:12][CH2:11][O:10][C:6](=[O:9])/[CH:7]=[CH:2]/[CH3:3])[CH3:16].[CH2:17]([O:18][CH2:19][CH2:20][O:21][C:11](=[O:10])[CH2:12][CH:1]=[CH2:2])[CH3:16]

Participants

7

Reactant 5

HCID 962WaterHCID 7850Allyl chlorideHCID 8076Glycol monoethyl ether2×HCID 14798Sodium HydroxideHCID 87901288HCID 87901288, compound

Product 2

HCID 15078144HCID 15078144, compoundYield 80%HCID 21316987HCID 21316987, compoundYield 12%

Procedure

In a manner similar to Example 1, 76.5 g of allyl chloride is reacted over a period of 4 hours, in the presence of 5 ml of Ni(CO)4, at 1.2 at. CO pressure and at a pH of 10.0, at 60° C., in 200 grams of ethyl glycol containing 0.14 wt.-% of H2O, with 1.12 moles of 20.4% sodium ethyl glycolate in ethyl glycol containing 0.31 wt.-% of NaOH. The distillate contains, according to gas chromatographic analysis (Hewlett-Packard, DC 200 silicone oil, length 4 m), 105 g of crotonic acid-2-ethoxyethylester (yield 80%) and 16 g of vinyl acetic acid-2-ethoxyethylester (yield 12%).

Workup

  1. customat 60° C.

Sources & evidence

ORD record
ord-059859b52f83443fa9e88088de374d3c
Source dataset
uspto-grants-1979_05
Patent number
US04156785

Reaction notes

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