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

HRID 34610Notes

Reaction equation

HRID 34610 reaction equation
[CH2:1]([C:4]1[C:11]([F:12])=[C:10]([F:13])[C:7]([CH2:8][OH:9])=[C:6]([F:14])[C:5]=1[F:15])[C:2]#[CH:3].[Cl-:16].[Li+].[ClH:18]>C(#N)C>[Cl:16]/[C:2](=[CH:3]\[Cl:18])/[CH2:1][C:4]1[C:5]([F:15])=[C:6]([F:14])[C:7]([CH2:8][OH:9])=[C:10]([F:13])[C:11]=1[F:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 114359092,3,5,6-Tetrafluoro-4-(2-propyn-1-yl)benzyl Alcohol

Product 1

HCID 13911484Z-4-(2,3-dichloroprop-2-en-1-yl)-2,3,5,6-tetrafluorobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(prop-2-yn-1-yl)-2,3,5,6-tetrafluorobenzyl alcohol (0.1 g) copper (II) chloride (1.3 g), and lithium chloride (0.62 g) in dry acetonitrile (23 cm3) was heated at the reflux temperature for 40 hours. The resulting dark solution was poured into dilute hydrochloric acid, and extracted into ethyl acetate. The organic phase was washed with more dilute hydrochloride acid, dried, and the solvent evaporated under reduced pressure to give Z-4-(2,3-dichloroprop-2-en-1-yl)-2,3,5,6-tetrafluorobenzyl alcohol (0.1 g) as an orange oil.

Workup

  1. extractionextracted into ethyl acetate
  2. washThe organic phase was washed with more dilute hydrochloride acid
  3. customdried
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-cc6c5d1acedf4d1b8e540664a279825e
Source dataset
uspto-grants-1988_08
Patent number
US04762835

Reaction notes

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