2-Chloroethanol → 1-[Bis(4-fluorophenyl)methoxy]-2-chloroethane

HRID 35296

Reaction equation

HRID 35296 reaction equation
[Cl:1][CH2:2][CH2:3][OH:4].S(=O)(=O)(O)O.[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)O)=[CH:13][CH:12]=1.O>C1C=CC=CC=1>[Cl:1][CH2:2][CH2:3][O:4][CH:17]([C:14]1[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=1)[C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 1230494,4'-Difluorobenzhydryl alcohol

Product 1

HCID 107793021-[Bis(4-fluorophenyl)methoxy]-2-chloroethane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 20 parts of 2-chloroethanol, 3 parts of sulfuric acid and 16 parts of benzene was heated on a water-bath. Then there were added dropwise 35 parts of 4-fluoro-α-(4-fluorophenyl)benzenemethanol dissolved in 32 parts of benzene. After the addition was complete, the whole was stirred and refluxed for 4 hours. After cooling the reaction mixture was poured into water. The benzene layer was separated, dried over calcium chloride and evaporated. The residue was distilled in vacuo, yielding 35 parts of 1,1'-[(2-chloroethoxy)methylene]bis[4-fluorobenzene]; bp. 164°-166° C. at 1.5 mm. pressure; nD20 : 1.5462; d2020 : 1.2290 (intermediate 1).

Workup

  1. temperaturewas heated on a water-bath
  2. additionAfter the addition
  3. temperaturerefluxed for 4 hours
  4. temperatureAfter cooling the reaction mixture
  5. customThe benzene layer was separated
  6. dry with materialdried over calcium chloride
  7. customevaporated
  8. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-aa649f34fbe0408682aae1bc3a34ceb5
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Linked notes

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