Acetic Acid → 2-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acid methyl ester

HRID 505663Notes

Reaction equation

HRID 505663 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[CH:18]=[C:17]([O:19][CH2:20][O:21][CH3:22])[CH:16]=[C:15]([O:23][CH2:24][O:25][CH3:26])[C:11]=1[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][Si](C=[N+]=[N-])(C)C.CCCCCC.C(O)(=O)C>CO>[CH3:27][O:13][C:12](=[O:14])[C:11]1[C:15]([O:23][CH2:24][O:25][CH3:26])=[CH:16][C:17]([O:19][CH2:20][O:21][CH3:22])=[CH:18][C:10]=1[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 68717409HCID 68717409, compoundHCID 86587183Trimethylsilyldiazomethane hexane

Product 1

HCID 687189312-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acid methyl esterYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above-obtained 2-(benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acid (20 mg, 0.054 mmol) was dissolved in methanol (2 mL) and the obtained solution was added with 2.0 mol/L trimethylsilyldiazomethane-hexane solution (0.30 mL, 0.60 mmol), followed by stirring at a room temperature for 1 hour. The reaction mixture was added with acetic acid (0.050 mL) and the solvent was evaporated under reduced pressure. The residue was purified by preparative thin-layer chromatography (chloroform/methanol=100/1) to obtain 2-(benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acid methyl ester (12 mg, 57%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by preparative thin-layer chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-127f354c8b9045fc8a77bc78e9f2e7ef
Source dataset
uspto-grants-2010_08
Patent number
US07781485B2

Reaction notes

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