Methanol → Methyl 3-(4-methylphenyl)-2-propenoate

HRID 1380932Notes

Reaction equation

HRID 1380932 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:9][C:8](=[O:10])[CH:7]=[CH:6][C:5]1[CH:11]=[CH:12][C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 158353-(p-Tolyl)acrylic acid

Product 1

HCID 589472Methyl 3-(4-methylphenyl)-2-propenoate

Procedure

A suspension of 300 g of p-methylcinnamic acid (J. Chem. Soc., Chem. Comm., 471, 1976) and 25 ml of concentrated sulfuric acid in 1.7 liters of methanol is heated to reflux for 24 hours. The solution is concentrated, cooled and filtered to give as a white solid, p-methylcinnamic acid methyl ester, mp 55°-56° C. NMR (DMSOd6) δ=7.36 (d, J=16 Hz, 1H); 7.36 (dd, J1 =30 Hz, J2 =7 Hz, 4H); 6.48 (d, J=16 Hz, 1H); 3.70 (s, 3H); 2.32 (s, 3H). IR (cm-1) 3061, 3028, 2949, 1713, 1634, 1607, 1570, 1516, 1438.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 24 hours
  3. concentrationThe solution is concentrated
  4. temperaturecooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-4ddab39f92da41a4a4fcb198f38ea8d4
Source dataset
uspto-grants-1986_04
Patent number
US04584313

Reaction notes

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