Hydrochloric Acid → 2,3,4,5,6-Pentafluorobenzyl Alcohol

HRID 1065602Notes

Reaction equation

HRID 1065602 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:9]([C:10](F)=[O:11])=[C:8]([F:13])[C:7]([F:14])=[C:6]([F:15])[C:5]=1[F:16].O.Cl>O1CCOCC1>[F:3][C:4]1[C:9]([CH2:10][OH:11])=[C:8]([F:13])[C:7]([F:14])=[C:6]([F:15])[C:5]=1[F:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 10910882HCID 10910882, compound

Product 1

HCID 99232,3,4,5,6-Pentafluorobenzyl AlcoholYield 211.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

38 g of sodium borohydride in 200 ml of dry dioxane are initially introduced into the apparatus at 20° C. and a solution of 86 g of pentafluorobenzoyl fluoride in 100 ml of dioxane is added dropwise, whilst stirring. When the addition has ended, the mixture is subsequently stirred at 20° C. for 2 hours and at 80° C. for 30 minutes and cooled and 75 ml of water are slowly added dropwise, followed by dilute hydrochloric acid until the mixture has a clearly acid reaction. After extraction with methylene chloride, the organic phase is distilled. 168 g of pentafluorobenzyl alcohol are obtained at a boiling point of 87° C./19 mbars.

Workup

  1. additionWhen the addition
  2. stirringthe mixture is subsequently stirred at 20° C. for 2 hours and at 80° C. for 30 minutes
  3. temperaturecooled
  4. customa clearly acid reaction
  5. extractionAfter extraction with methylene chloride
  6. distillationthe organic phase is distilled

Sources & evidence

ORD record
ord-978854d82b1d46a1af81cc5e781ee35f
Source dataset
uspto-grants-1982_05
Patent number
US04330366

Reaction notes

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