Hydrochloric Acid → 2,3,5,6-Tetrafluoro-4-(2-propyn-1-yl)benzyl Alcohol

HRID 34601Notes

Reaction equation

HRID 34601 reaction equation
[CH2:1]([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])[C:2]#[CH:3].Cl>CO>[CH2:1]([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])[C:2]#[CH:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13670573HCID 13670573, compound

Product 1

HCID 114359092,3,5,6-Tetrafluoro-4-(2-propyn-1-yl)benzyl AlcoholYield 86.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-[4-(prop-2-yn-1-yl)-2,3,5,6-tetrafluorobenzyloxy]tetrahydropyran (0.8 g), dilute hydrochloric acid (2N, 5 cm3) and methanol (30 cm3) was stirred together at the ambient temperature for 2 hours, after which the more volatile portion was removed by evaporation under reduced pressure. The residue was extracted with diethyl ether, the extracts combined, washed with water, and dried over anhydrous magnesium sulphate. Removal of the solvent by evaporation under reduced pressure yielded an oil which crystallised on standing to give 4-(prop-2-yn-1-yl)-2,3,5,6-tetrafluorobenzyl alcohol (0.5 g), m.p. 51°-52° C., after recrystallisation from petroleum ether (boiling range 60°-80° C.).

Workup

  1. customafter which the more volatile portion was removed by evaporation under reduced pressure
  2. extractionThe residue was extracted with diethyl ether
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customRemoval of the solvent
  6. customby evaporation under reduced pressure
  7. customyielded an oil which
  8. customcrystallised

Sources & evidence

ORD record
ord-4e1cf2f80a354c1a9845a67b220d0b6e
Source dataset
uspto-grants-1988_08
Patent number
US04762835

Reaction notes

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