Ethanol → 4-Methoxybenzoylacetonitrile

HRID 46560

Reaction equation

HRID 46560 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].C(O)C.[C-:16]#[N:17].[Na+]>O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([CH2:2][C:16]#[N:17])=[O:4])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 8929Sodium Cyanide

Product 1

HCID 2333984-Methoxybenzoylacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 25.0 g. portion of α-bromo-p-methoxyacetophenone is suspended in 125 ml. of ethanol. A solution of 16.0 g. of sodium cyanide in 75 ml. of water is added, using an ice-water bath to keep the temperature at 25°-30° C. The mixture is stirred for 45 minutes at room temperature. A total of 1.2 liters of water is added in 200 ml. increments with filtration through celite until no more precipitate forms. The filtrate is acidified to pH 5 with acetic acid. The solid is collected, washed with water, dried and recrystallized from benzene giving p-methoxybenzoylacetonitrile.

Workup

  1. customat 25°-30° C
  2. filtrationincrements with filtration through celite until no more precipitate forms
  3. customThe solid is collected
  4. washwashed with water
  5. customdried
  6. customrecrystallized from benzene

Sources & evidence

ORD record
ord-1edd1f6c04144de49225fd4a46496de2
Source dataset
uspto-grants-1979_11
Patent number
US04173650

Linked notes

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