Potassium Cyanide → 2-(3-Difluoromethoxyphenyl)-2-hydroxyacetonitrile

HRID 1438170

Reaction equation

HRID 1438170 reaction equation
[F:1][CH:2]([F:12])[O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8].[C-:13]#[N:14].[K+].OS([O-])=O.[Na+]>C(OCC)(=O)C.O>[F:1][CH:2]([F:12])[O:3][C:4]1[CH:5]=[C:6]([CH:7]([OH:8])[C:13]#[N:14])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 27369853-(Difluoromethoxy)benzaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 544938472-(3-Difluoromethoxyphenyl)-2-hydroxyacetonitrileYield 92.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3-difluoromethoxybenzaldehyde (1.77 g, 10 mmol) in ethyl acetate (25 mL) was added a solution of KCN (2.0 g) and NaHSO3 (3.2 g) dissolved in H2O (25 mL). It was left stirring overnight before it was extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried and concentrated. The crude product was purified by silica gel chromatography to give 131A (1.85 g, 92% yield) as an oil.

Workup

  1. waitIt was left
  2. extractionwas extracted with ethyl acetate (2×50 mL)
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6d746ab88683482984bcbc8e121a4e74
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Linked notes

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