Acetyl chloride → Methyl 3-(3,4-dimethoxyphenyl)propanoate

HRID 1031790Notes

Reaction equation

HRID 1031790 reaction equation
[C:1](Cl)(=O)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]>CO.COC(COC)C>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:15][CH2:16][C:17]([O:19][CH3:1])=[O:18])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 750193-(3,4-Dimethoxyphenyl)propionic acid

Product 1

HCID 520347Methyl 3-(3,4-dimethoxyphenyl)propanoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 24509Propylene glycol dimethyl etherSolvent

Procedure

Acetyl chloride (20 cc) was added dropwise over 10 minutes with stirring to methanol (400 cc); the resulting solution was added all at once to a magnetically stirred suspension of 3-(3,4-dimethoxyphenyl)propionic acid (500 g, 2.378 moles) in methanol (1.6 1) and 2,3-dimethoxypropane (250 cc). The reaction mixture was stirred overnight at room temperature and then at reflux for 1 hour. After cooling, the solution was evaporated in vacuo to a light yellow syrup; yield: 533 g (100%).

Workup

  1. additionthe resulting solution was added all at
  2. temperatureat reflux for 1 hour
  3. temperatureAfter cooling
  4. customthe solution was evaporated in vacuo to a light yellow syrup

Sources & evidence

ORD record
ord-5a584d9fe4e149928eb222db2d7489b5
Source dataset
uspto-grants-1990_09
Patent number
US04954659

Reaction notes

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