Water → 4-(2-Chloroprop-2-en-1-yl)-2,3,5,6-tetrafluorobenzyl alcohol

HRID 654615Notes

Reaction equation

HRID 654615 reaction equation
[Cl:1][C:2](=[CH2:22])[CH2:3][C:4]1[C:17]([F:18])=[C:16]([F:19])[C:7]([CH2:8][O:9]C2CCCCO2)=[C:6]([F:20])[C:5]=1[F:21].O>CO.Cl>[Cl:1][C:2](=[CH2:22])[CH2:3][C:4]1[C:5]([F:21])=[C:6]([F:20])[C:7]([CH2:8][OH:9])=[C:16]([F:19])[C:17]=1[F:18]

Participants

5

Reactant 2

HCID 962WaterHCID 13911479HCID 13911479, compound

Product 1

HCID 139114804-(2-Chloroprop-2-en-1-yl)-2,3,5,6-tetrafluorobenzyl alcoholYield 99.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

The tetrahydropyranyl ether prepared in stage (i) (0.2 g), was dissolved in methanol (6 cm3), and to the stirred solution was added concentrated hydrochloric acid (several drops). After stirring for 6 hours, and standing for a further 14 hours, the reaction mixture was poured into water, and extracted into ethyl acetate. The organic layer was washed with water and brine, dried, and the solvent evaporated under reduced pressure to give 4-(2-chloroprop-2-en-1-yl)-2,3,5,6-tetrafluorobenzyl alcohol as an orange oil (0.15 g).

Workup

  1. waitstanding for a further 14 hours
  2. extractionextracted into ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-9fe750ce504146e3841a9c63be6d7a98
Source dataset
uspto-grants-1992_07
Patent number
US05132469

Reaction notes

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