Water → 2,2,2-Trichloroethyl 2,4-bis(trichloromethyl)benzo[1,3]dioxin-6-carboxylate

HRID 224389Notes

Reaction equation

HRID 224389 reaction equation
[Cl:1][C:2]([Cl:21])([Cl:20])[CH:3]1[O:8][CH:7]([C:9]([Cl:12])([Cl:11])[Cl:10])[C:6]2[CH:13]=[C:14]([C:17](Cl)=[O:18])[CH:15]=[CH:16][C:5]=2[O:4]1.[Cl:22][C:23]([Cl:27])([Cl:26])[CH2:24]O.[OH2:28]>>[Cl:21][C:2]([Cl:1])([Cl:20])[CH:3]1[O:8][CH:7]([C:9]([Cl:10])([Cl:11])[Cl:12])[C:6]2[CH:13]=[C:14]([C:17]([O:18][CH2:24][C:23]([Cl:27])([Cl:26])[Cl:22])=[O:28])[CH:15]=[CH:16][C:5]=2[O:4]1

Participants

4

Reactant 3

HCID 962WaterHCID 8259TrichloroethanolHCID 233329602,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxine-6-carbonyl chloride

Product 1

HCID 233329482,2,2-Trichloroethyl 2,4-bis(trichloromethyl)benzo[1,3]dioxin-6-carboxylate

Procedure

A mixture of 2,4-bis(trichloromethyl)benzo[1,3]dioxin-6-carbonyl chloride (5.0 g.) and 2,2,2-trichloroethanol (25 ml.) was warmed on a steam bath for 2 hours. The reaction mixture was cooled, and water was added to produce a white precipitate which was filtered off and crystallised from a mixture of ether and petroleum ether (b.p. 60°-80° C.) to give 2,2,2-trichloroethyl 2,4-bis(trichloromethyl)benzo[1,3]dioxin-6-carboxylate, m.p. 129°-130° C.

Workup

  1. temperaturewas warmed on a steam bath for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. customto produce a white precipitate which
  4. filtrationwas filtered off
  5. customcrystallised from a mixture of ether and petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-ce9dcc0902704167ad3ec2b9c5b30a8e
Source dataset
uspto-grants-1980_11
Patent number
US04232032

Reaction notes

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