Hydrochloric Acid → Z-4-(3-chloroprop-2-en-1-yl)-2,3,5,6-tetrafluorobenzyl alcohol

HRID 34608Notes

Reaction equation

HRID 34608 reaction equation
[Cl:1][CH:2]=[CH:3][CH2:4][C:5]1[C:18]([F:19])=[C:17]([F:20])[C:8]([CH2:9][O:10]C2CCCCO2)=[C:7]([F:21])[C:6]=1[F:22].Cl>CO.O>[Cl:1]/[CH:2]=[CH:3]\[CH2:4][C:5]1[C:6]([F:22])=[C:7]([F:21])[C:8]([CH2:9][OH:10])=[C:17]([F:20])[C:18]=1[F:19]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54011856HCID 54011856, compound

Product 1

HCID 13911478Z-4-(3-chloroprop-2-en-1-yl)-2,3,5,6-tetrafluorobenzyl alcohol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The tetrahydropyranyl ether prepared in stage (ii) was dissolved in methanol (30 cm3), and to the stirred solution was added a catalytic amount of concentrated hydrochloric acid. After stirring for two hours, the reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed and dried, and the solvent evaporated under reduced pressure to give Z-4-(3-chloroprop-2-en-1-yl)-2,3,5,6-tetrafluorobenzyl alcohol (0.6 g) as a colourless oil, which solidified on standing.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed
  3. customdried
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-df994d04c0054c998bbdfece7eb174fb
Source dataset
uspto-grants-1988_08
Patent number
US04762835

Reaction notes

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