Water → HCID 22054213, compound

HRID 1830232Notes

Reaction equation

HRID 1830232 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[CH:8]=[CH:9][C:10]([OH:16])=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13].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[CH:8]=[CH:9][C:10]([O:16][C:28](=[O:30])[CH3:29])=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13]

Participants

4

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 22054252HCID 22054252, compound

Product 1

HCID 22054213HCID 22054213, compoundYield 68%

Conditions

Temperature
65 °C

Procedure

5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-hydroxybenzoic acid (1.30 g, 3.59 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=10:1) to obtain the titled compound (0.99 g, 2.45 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=10:1)

Sources & evidence

ORD record
ord-86eff99952074d3fbdd2538b4f663e77
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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