Hydrochloric Acid → HCID 13911483, compound

HRID 654617Notes

Reaction equation

HRID 654617 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]>[Cu](Cl)Cl.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

6

Reactant 3

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

Product 1

HCID 13911483HCID 13911483, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(prop-2-yn-1-yl)-2,3,5,6-tetrafluorobenzyl alcohol (0.1 g), copper (II) chloride (1.3 g), lithium chloride (0.62 g) and 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 hydrochloric acid, dried, and the solvent evaporated under reduced pressure to give E-4-(2,3-dichloroprop-2-en-1-yl)-2,3,5,6-tetrafluorobenzyl alcohol (0.1 g) as an orange oil.

Workup

  1. temperaturewas heated at the reflux temperature for 40 hours
  2. extractionextracted into ethyl acetate
  3. washThe organic phase was washed with more dilute hydrochloric acid
  4. customdried
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-cd7e257254a4496e95d7da30f985169a
Source dataset
uspto-grants-1992_07
Patent number
US05132469

Reaction notes

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