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

HRID 964650Notes

Reaction equation

HRID 964650 reaction equation
[F: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].[CH3:13]O.S(Cl)(Cl)=O>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([O:8][CH3:13])=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 679773-(2-Fluorophenyl)prop-2-enoic acid

Product 1

HCID 14816712-Propenoic acid, 3-(2-fluorophenyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

15 gm of 2-fluorocinnamic acid was suspended into 100 ml of methanol. While maintaining the suspension at 0° C., 1.7 gm of thionyl chloride was added slowly. After the addition, the mixture was stirred for 30 minutes at 0° C. and for 4 hour at room temperature. The residue obtained by the removal of the solvent was subjected to silica gel column chromatography using chloroform as an eluant to obtain fractions containing the target compound. The fractions were concentrated to produce 17.8 gm of the title compound.

Workup

  1. additionAfter the addition
  2. customThe residue obtained by the removal of the solvent
  3. customto obtain fractions
  4. additioncontaining the target compound
  5. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-49a5df311acd46e18a936b64a1e0e97b
Source dataset
uspto-grants-1998_06
Patent number
US05770605

Reaction notes

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