Potassium Carbonate → 2-(2-Formyl-6-methylphenoxy)acetonitrile

HRID 2117232Notes

Reaction equation

HRID 2117232 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:12][C:13]#[N:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOCC>[C:13]([CH2:12][O:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])#[N:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 5227773-Methylsalicylaldehyde

Product 1

HCID 222413452-(2-Formyl-6-methylphenoxy)acetonitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 2-hydroxy-3-methylbenzaldehyde (10.2 g, 75.0 moles, Aldrich), bromoacetonitrile (5.70 mL, 82.5 mmoles), and potassium carbonate (11.4 g, 82.5 mmoles) in DMF (150 mL) is heated to 55° C. for 3 hours, cooled, then diluted with ether. The mixture is washed with distilled water, saturated NaCl solution, then the organic layer dried over MgSO4 and concentrated to give the title compound as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 10.20 (s, 1H), 7.70 (d, 1H), 7.53 (d, 1H), 7.29 (m, 1H), 4.81 (s, 2H), 2.42 (s, 3H).

Workup

  1. temperaturecooled
  2. washThe mixture is washed with distilled water, saturated NaCl solution
  3. dry with materialthe organic layer dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ce742649d16d40d9b48008dcd626b4d4
Source dataset
uspto-grants-2008_10
Patent number
USRE040558E1

Reaction notes

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