Triethyl phosphite → 2,4,4-Trichlorobutadienyl diethyl phosphate

Reaction equation

[Cl:1][C:2](Cl)([CH:5]=[C:6]([Cl:8])[Cl:7])[CH:3]=[O:4].[P:10]([O:17]CC)([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]>>[P:10]([O:14][CH2:15][CH3:16])([O:11][CH2:12][CH3:13])([O:4][CH:3]=[C:2]([Cl:1])[CH:5]=[C:6]([Cl:8])[Cl:7])=[O:17]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 1088492,2,4,4-Tetrachloro-3-butenal

Product 1

HCID 30178092,4,4-Trichlorobutadienyl diethyl phosphateYield 62.8%

Procedure

184 g of 2,2,4,4-tetrachloro-but-3-enal (prepared in accordance with Example 6) were reacted in a manner analogous to that described in Example 6 with 166 g of triethyl phosphite, and 172 g of product were obtained by distillation at 0.2 to 0.3 torr and 121° to 125° C. NMR-spectrum : δ (CH3) : 1.33 ppm, J = 7 Hz; δ (CH2) : 3.95 - 4.47 ppm; δ (C=CH-C) : 6.67 ppm; δ (CH-O-P) : 7.33 ppm, J = 6 Hz.

Sources & evidence

ORD record: ord-fda07e5a7194441ba890858b352e053f
Source dataset: uspto-grants-1977_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04017613

Reaction notes

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