1,1,1,2-Tetrachloro-2,2-difluoroethane → 3,3-Dimethyl-4,6,6,7-tetrachloro-7,7-difluoroenanthic acid methyl ester

HRID 1277989

Reaction equation

HRID 1277989 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][C:5]([CH3:9])([CH3:8])[CH:6]=[CH2:7].[Cl:11][C:12](Cl)([Cl:17])[C:13]([Cl:16])([F:15])[F:14].C1(C(C(C2C=CC=CC=2)O)=O)C=CC=CC=1.[ClH:35].CNC>C(#N)C>[CH3:1][O:2][C:3](=[O:10])[CH2:4][C:5]([CH3:9])([CH3:8])[CH:6]([Cl:35])[CH2:7][C:12]([Cl:17])([Cl:11])[C:13]([Cl:16])([F:15])[F:14]

Participants

6

Reactant 4

HCID 64261,1,1,2-Tetrachloro-2,2-difluoroethaneHCID 8400BenzoinHCID 10473Dimethylamine, hydrochlorideHCID 114129Methyl 3,3-dimethyl-4-pentenoate

Product 1

HCID 155750363,3-Dimethyl-4,6,6,7-tetrachloro-7,7-difluoroenanthic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

37.5 g of 3,3-dimethyl-4-pentenoic acid methyl ester, 102 g of 1,1,1,2-tetrachloro-2,2-difluoroethane, 22 g of acetonitrile, 325 mg of FeCl3.6H2O, 255 mg of benzoin and 200 mg of dimethylamine hydrochloride were heated to 100°-120° C. in a 250 ml VA autoclave under 6 bars of nitrogen for 7 hours. Distillation of the mixture gave 3,3-dimethyl-4,6,6,7-tetrachloro-7,7-difluoroenanthic acid methyl ester of boiling point 129°-134° C./0.7-0.9 m bar. Refractive index: nD20 =1.4680. ##STR8##

Workup

  1. distillationDistillation of the mixture

Sources & evidence

ORD record
ord-8d9c87fbabdc48cfa957e9862b8938dc
Source dataset
uspto-grants-1981_07
Patent number
US04279923

Linked notes

Loading…