Methanol → 2-Propenoic acid, 3-(2-methylphenyl)-, methyl ester, (2E)-

HRID 1805945Notes

Reaction equation

HRID 1805945 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].S(Cl)(Cl)=O.[CH3:17]O>>[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1/[CH:4]=[CH:5]/[C:6]([O:8][CH3:17])=[O:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 983063-(2-Methylphenyl)prop-2-enoic acid

Product 1

HCID 101763492-Propenoic acid, 3-(2-methylphenyl)-, methyl ester, (2E)-

Conditions

Temperature
60 °C

Procedure

To 2-Methylcinnamic acid (5.68 g, 35 mmol) in MeOH (175 ml) was added thionyl chloride (2.55 ml, 35.0 mmol) dropwise. The resulting solution was stirred for 10 hours at 60° C. The solution was cooled to room temperature and concentrated. The crude ester was dissolved in CH2Cl2 and washed twice with saturated NaHCO3. The organics were combined, dried, and concentrated affording 6.45 g of methyl(2E)-3-(2-methylphenyl)acrylate.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. concentrationconcentrated
  3. dissolutionThe crude ester was dissolved in CH2Cl2
  4. washwashed twice with saturated NaHCO3
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-20814bd0e025441892d025c5fc008e97
Source dataset
uspto-grants-2013_01
Patent number
US08354545B2

Reaction notes

Loading…