Hydrochloric Acid → HCID 13911483, compound

HRID 2051249Notes

Reaction equation

HRID 2051249 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-755803e895384c7380f4546807ca05e1
Source dataset
uspto-grants-1991_05
Patent number
US05017606

Reaction notes

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