1,1,1-Trichloro-2,2,2-trifluoroethane → (2,2-Dichloro-3,3,3-trifluoro-1-hydroxypropyl)-2,3-dichlorobenzene

HRID 1607908Notes

Reaction equation

HRID 1607908 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Cl:11][C:12](Cl)([Cl:17])[C:13]([F:16])([F:15])[F:14]>CN(C=O)C.Cl.[Zn]>[Cl:11][C:12]([Cl:17])([C:13]([F:16])([F:15])[F:14])[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([Cl:10])[C:2]=1[Cl:1])[OH:5]

Participants

6

Reactant 2

HCID 96351,1,1-Trichloro-2,2,2-trifluoroethaneHCID 357452,3-Dichlorobenzaldehyde

Product 1

HCID 19849825(2,2-Dichloro-3,3,3-trifluoro-1-hydroxypropyl)-2,3-dichlorobenzene

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 35.0 g of 2,3-dichlorobenzaldehyde, 41.2 g of 1,1,1-trichloro-2,2,2-trifluoroethane and 16.4 g of zinc powder in 360 ml of DMF is stirred for 66 h at RT, and subsequently taken up in a mixture of 600 ml of 10% hydrochloric acid and 600 g of ice. By extraction with ether, drying, and concentration of the organic extracts by evaporation, there is obtained (2,2-dichloro-3,3,3-trifluoro-1-hydroxypropyl)-2,3-dichlorobenzene in the form of a yellow oil (compound No. 5.10).

Workup

  1. extractionBy extraction with ether
  2. customdrying
  3. customconcentration of the organic extracts by evaporation

Sources & evidence

ORD record
ord-5563e6ed49ac415bbf8d54ec1bbd8895
Source dataset
uspto-grants-1989_09
Patent number
US04868202

Reaction notes

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