Methanol → methyl (2E)-3-(4-formylphenyl)prop-2-enoate

HRID 2098563Notes

Reaction equation

HRID 2098563 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1)=[O:2].OS(O)(=O)=O.[CH3:19]O>>[CH:1]([C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:19])=[O:12])=[CH:5][CH:4]=1)=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 53572804-FORMYLCINNAMIC ACID

Product 1

HCID 11008713methyl (2E)-3-(4-formylphenyl)prop-2-enoateYield 86%

Conditions

Temperature
5 °C

Procedure

A suspension of (E)-3-(4-formylphenyl)acrylic acid (2 g, 10.5 mmol) in methanol (30 mL) was cooled to 5° C. and then concentrated H2SO4 (3 mL) was added under stirring and heated at 60° C. for 2 hours. The solvent was removed by evaporation and the obtained compound was stirred with water (100 mL) for 15 minutes. The precipitated white solid was filtered, washed with water (300 mL) and dried to get the pure product (1.9 g, 86% yield).

Workup

  1. temperatureheated at 60° C. for 2 hours
  2. customThe solvent was removed by evaporation
  3. stirringthe obtained compound was stirred with water (100 mL) for 15 minutes
  4. filtrationThe precipitated white solid was filtered
  5. washwashed with water (300 mL)
  6. customdried

Sources & evidence

ORD record
ord-8acf366fcfc4425c95454121231f3caf
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

Loading…