Chloroacetonitrile → HCID 13961736, compound

HRID 256339Notes

Reaction equation

HRID 256339 reaction equation
[OH:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:14](=O)([O-])[O-].[K+].[K+].Cl[CH2:21][C:22]#[N:23]>CN(C)C=O>[C:22]([CH2:21][CH2:14][O:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])#[N:23]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 80651Methyl 3-methoxysalicylate

Product 1

HCID 13961736HCID 13961736, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 57.1 g (0.31 mole) of 2-hydroxy-3-methoxybenzoic acid, methyl ester, 95.5 g (0.69 mole) of anhydrous potassium carbonate, and 23.9 ml (28.5 g; 0.38 mole) of chloroacetonitrile in 260 ml of N,N-dimethylformamide is heated on the steam bath for three hours. The mixture is cooled, added to 1700 g of ice/water, stirred for 1 hour, and the precipitated crude product is filtered and washed with water. Recrystallization from aqueous methanol yields 52.5 g 77% yield) of the 2-cyanoethoxy-3-methoxybenzoic acid, methyl ester, mp 77°-78° C. (See U.S. Pat. No. 4,420,476 for mp of 74°-75° C.)

Workup

  1. temperatureis heated on the steam bath for three hours
  2. temperatureThe mixture is cooled
  3. customthe precipitated crude product
  4. filtrationis filtered
  5. washwashed with water
  6. customRecrystallization from aqueous methanol

Sources & evidence

ORD record
ord-c202b639c696456fb101ec787bee625b
Source dataset
uspto-grants-1987_10
Patent number
US04703053

Reaction notes

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