Acetyl chloride → 3-(3-Nitrophenyl)acrylic acid methyl ester

HRID 351065Notes

Reaction equation

HRID 351065 reaction equation
[C:1](Cl)(=O)C.[N+:5]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]([OH:18])=[O:17])[CH:11]=[CH:12][CH:13]=1)([O-:7])=[O:6]>CO>[CH3:1][O:17][C:16](=[O:18])[CH:15]=[CH:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([N+:5]([O-:7])=[O:6])[CH:9]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 683902-Propenoic acid, 3-(3-nitrophenyl)-

Product 1

HCID 1018253-(3-Nitrophenyl)acrylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (6.5 ml, 0.09 mol) was added dropwise to methanol (130 ml) at −15° C. temperature. The reaction mixture was stirred for 30 min. simultaneously allowing to warm up to 0° C. 3-(3-Nitro-phenyl)-acrylic acid (21) (25 g, 0.13 mol) was added by small portions to the mixture at 0° C. and the resulting reaction mixture was stirred overnight at ambient temperature. The forming precipitate was filtered, washed with methanol and dried affording the title compound in a form of white crystals (26.58 g, 98%).

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred overnight at ambient temperature
  3. filtrationThe forming precipitate was filtered
  4. washwashed with methanol
  5. customdried

Sources & evidence

ORD record
ord-d01f8c25fc804c98bebd1c3c19691129
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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