Water → HCID 22054188, compound

HRID 1830233Notes

Reaction equation

HRID 1830233 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:26])=[C:5]([C:17]([O:24][CH3:25])=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[CH2:6][C:7]1[C:8]([OH:16])=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11].O.[C:28](OC(=O)C)(=[O:30])[CH3:29]>>[CH3:1][O:2][C:3]1[C:4]([CH3:26])=[C:5]([C:17]([O:24][CH3:25])=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[CH2:6][C:7]1[C:8]([O:16][C:28](=[O:30])[CH3:29])=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 22054235HCID 22054235, compound

Product 1

HCID 22054188HCID 22054188, compoundYield 68%

Conditions

Temperature
65 °C

Procedure

3-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-hydroxybenzoic acid (0.288 g, 0.795 mmol) was dissolved in acetic anhydride (5 ml) and the resulting solution was stirred under heating at 65° C. for 3 hours. The reaction solution was cooled and after adding thereto water (20 ml) and stirring at room temperature for 1 hour, extracted with ethyl acetate. The extract was washed with saturated brine and then dried, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography (chloroform:methanol=9:1) to obtain the titled compound (0.245 g, 0.541 mmol, 68%).

Workup

  1. temperatureThe reaction solution was cooled
  2. additionafter adding
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. customdried
  6. customthe solvent was removed by distillation
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-54de1857d5a34fba9464bc9a8ca09e43
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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