1-Chloro-4-(chloromethyl)benzene → HCID 13384258, compound

HRID 973290Notes

Reaction equation

HRID 973290 reaction equation
[OH:1][C:2]([C:12]([F:15])([F:14])[F:13])([C:8]([F:11])([F:10])[F:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>CN(C)C=O>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][O:1][C:2]([C:8]([F:11])([F:10])[F:9])([C:12]([F:13])([F:14])[F:15])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 13384220HCID 13384220, compound

Product 1

HCID 13384258HCID 13384258, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-hydroxy-3,3,3-trifluoro-2-trifluoromethylpropionate (12.0 g.) is added dropwise at ambient temperature to a stirred mixture of sodium hydride (2.4 g. of a 60% dispersion in oil) and dimethylformamide (100 ml.). The mixture is stirred for 4 hours, 4-chlorobenzyl chloride (8.4 g.) is added, and the stirring is continued for 6 days. The mixture is filtered, and the filtrate is evaporated in vacuo. The residue is fractionally distilled at 0.1 mm. pressure, collecting the fraction, (9.9 g.) b.p. 78°-80° C., m.p. 32°-33° C, which is crystallized from pentane to give ethyl 2-(4-chlorobenzyloxy)-3,3,3-trifluoro-2-trifluoromethylpropionate, m.p. 33° C.

Workup

  1. waitthe stirring is continued for 6 days
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated in vacuo
  4. distillationThe residue is fractionally distilled at 0.1 mm
  5. custompressure, collecting the fraction, (9.9 g.) b.p. 78°-80° C., m.p. 32°-33° C, which
  6. customis crystallized from pentane

Sources & evidence

ORD record
ord-21089d16163d49eaa19ca56703c7f452
Source dataset
uspto-grants-1977_10
Patent number
US04055595

Reaction notes

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