4-Fluoro-3-phenoxybenzaldehyde → (4-Fluoro-3-phenoxyphenyl)methanol

HRID 247663Notes

Reaction equation

HRID 247663 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[BH4-].[Na+]>C(O)C.C(OCC)C.Cl>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 1100684-Fluoro-3-phenoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 12874224(4-Fluoro-3-phenoxyphenyl)methanol

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Under argon 2.16 g (0.010 mole) of 4-fluoro-3-phenoxybenzaldehyde was dissolved in 50 ml of absolute ethanol. To this solution was added with stirring 0.28 g (0.0074 mole) of sodium borohydride. After stirring at room temperature for 24 hours, 3 ml of 10% hydrochloric acid was added to the reaction mixture. The solvent was then evaporated under reduced pressure, leaving a milky-white residue. This residue was dissolved in 100 ml of diethyl ether and 5% hydrochloric acid. The organic phase was separated, washed in succession twice with 25 ml of 5% hydrochloric acid and twice with 10 ml of a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, leaving 1.98 g of (4-fluoro-3-phenoxyphenyl)methyl alcohol as a clear, colorless liquid. The nmr and ir spectra were consistent with the proposed structure.

Workup

  1. additionTo this solution was added
  2. customThe solvent was then evaporated under reduced pressure
  3. customleaving a milky-white residue
  4. customThe organic phase was separated
  5. washwashed in succession twice with 25 ml of 5% hydrochloric acid and twice with 10 ml of a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e79f26c889de44d6b08039cb4f4d3011
Source dataset
uspto-grants-1987_11
Patent number
US04709068

Reaction notes

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