Sodium Cyanide → 2-(4-Fluoro-3-phenoxyphenyl)-2-hydroxyacetonitrile

HRID 903835Notes

Reaction equation

HRID 903835 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.[C-:17]#[N:18].[Na+].S(=O)(O)[O-].[Na+]>CCOCC.O>[C:17]([CH:6]([OH:7])[C:5]1[CH:8]=[CH:9][C:2]([F:1])=[C:3]([O:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:4]=1)#[N:18]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 1100684-Fluoro-3-phenoxybenzaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 103771092-(4-Fluoro-3-phenoxyphenyl)-2-hydroxyacetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-fluoro-3-phenoxybenzaldehyde (0.39 g, 1.8 mmol) in 25 ml of ether is added 25 ml of water followed by sodium cyanide (0.149 g, 3.04 mmol). The mixture is stirred vigorously while a solution of sodium bisulfite (0.257 g, 2.47 mmol) in 15 ml of water is added over about 5 minutes. The reaction mixture is stirred for two hours. The organic phase is separated, washed with water, dried over calcium sulfate and solvent evaporated to give α-cyano-4-fluoro-3-phenoxybenzyl alcohol.

Workup

  1. additionis added over about 5 minutes
  2. customThe organic phase is separated
  3. washwashed with water
  4. dry with materialdried over calcium sulfate and solvent
  5. customevaporated

Sources & evidence

ORD record
ord-8e79ca732573420ebece7c173b397324
Source dataset
uspto-grants-1980_10
Patent number
US04229368

Reaction notes

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