Methanol → HCID 86748762, compound

HRID 1647223Notes

Reaction equation

HRID 1647223 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11](=[O:23])[CH:12]=[CH:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([OH:19])=[O:18].S(=O)(=O)(O)O.[CH3:29]O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11](=[O:23])[CH:12]=[CH:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([O:19][CH3:29])=[O:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 54509153HCID 54509153, compound

Product 1

HCID 86748762HCID 86748762, compound

Procedure

A solution of 3-[3-(2,5-dimethoxyphenyl)-3-oxo-1-propenyl]-benzoic acid (2.86 g, 9.15 mmol) in methanol (200 mL) is treated with sulfuric acid (0.5 mL) and heated under reflux for 6 hours. After standing at room temperature 12 hours, the resulting solid is collected by filtration and washed with methanol to provide 2.2 g of the title compound; mp 108°-110° C. Additional material (0.7 g) is obtained by concentrating the filtrate and washings under vacuum, partitioning the residue between saturated sodium bicarbonate solution and dichloromethane, and concentrating the dried (MgSO4) organic layer to dryness.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. filtrationthe resulting solid is collected by filtration
  4. washwashed with methanol

Sources & evidence

ORD record
ord-34bf6d720ae24662923bdee9bb28cff1
Source dataset
uspto-grants-1995_07
Patent number
US05430047

Reaction notes

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