Acetic Acid → HCID 21919190, compound

HRID 1245159Notes

Reaction equation

HRID 1245159 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:33])=[C:5]([C:24]([O:31][CH3:32])=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:8]=1.[CH3:34][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>CO>[CH3:1][O:2][C:3]1[C:4]([CH3:33])=[C:5]([C:24]([O:31][CH3:32])=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:13][CH3:34])=[O:12])=[C:9]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 10275809HCID 10275809, compound

Product 1

HCID 21919190HCID 21919190, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic acid (525 mg, 1.1615 mmol) was dissolved in methanol (20 ml), trimethylsilyl diazomethane (15.9 g, 10% solution in hexane, 13.9473 mmol) was added thereto under cooling with ice and the mixture was stirred at room temperature for 2 hours. To the reaction solution was added acetic acid (2 ml) and the mixture was allowed to stand so as to decompose an excessive reagent. The reaction solution was concentrated to give the title compound (530 mg, 1.1373 mmol, 98%).

Workup

  1. temperatureunder cooling with ice
  2. concentrationThe reaction solution was concentrated

Sources & evidence

ORD record
ord-0264d74cbdbd485dba184fc7f77de829
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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