Hydrochloric Acid → HCID 14517058, compound

HRID 1614453Notes

Reaction equation

HRID 1614453 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11].[BH4-].[Na+].Cl>CO.O>[F:3][C:4]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH2:10][OH:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 14517057HCID 14517057, compound

Product 1

HCID 14517058HCID 14517058, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydroxide solution (2 molar, 0.5 cm3) was added to a solution of 3-(2,4-difluorophenoxy)benzaldehyde (2 g) in methanol (20 cm3) and the mixture was cooled to 0° C. Sodium borohydride (0.5 g) was added, and the mixture stirred for 30 minutes. After this time, water was added, and the mixture acidified to pH 4 by addition of dilute hydrochloric acid. This mixture was extracted with diethyl ether (5×50 cm3). The combined organic layers were dried over anhydrous sodium sulphate, and the solvents evaporated under reduced pressure. The residue was purified by column chromatography on a silica gel support, using n-hexane containing 20% by volume ethyl acetate as eluent, to give 3-(2,4-difluorophenoxy)benzyl alcohol as a colourless oil.

Workup

  1. extractionThis mixture was extracted with diethyl ether (5×50 cm3)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  3. customthe solvents evaporated under reduced pressure
  4. customThe residue was purified by column chromatography on a silica gel support

Sources & evidence

ORD record
ord-886b37d59cbf4688955afbc3c2c77eaa
Source dataset
uspto-grants-1993_03
Patent number
US05196610

Reaction notes

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