2,6-Diacetoxybenzoic acid → Methyl 2,6-diacetoxybenzoate

HRID 1267828Notes

Reaction equation

HRID 1267828 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15](=[O:17])[CH3:16])[C:6]=1[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].[C:18]1(C)C=CC=CC=1.CO.[Si](C=[N+]=[N-])(C)(C)C.CCCCCC>CCCCCC>[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15](=[O:17])[CH3:16])[C:6]=1[C:7]([O:9][CH3:18])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 100074062,6-Diacetoxybenzoic acidHCID 21867641Toluene methanolHCID 86587183Trimethylsilyldiazomethane hexane

Product 1

HCID 14343346Methyl 2,6-diacetoxybenzoate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a stirred 4° solution of Part B 2,6-diacetoxybenzoic acid (5.8 g, mmol) in 4:1 PhMe/MeOH (25 mL) was added 17 mL of 2M TMSCHN2/hexane over 10 min. After tlc analysis (1:1 ETOAc/hexane) revealed complete conversion, the volatiles were removed using a rotary evaporator and the residue purified by silica gel chromatography. 1:1 CH2Cl2/hexane-CH2Cl2 eluted 4.5 g of methyl 2,6-diacetoxybenzoate.

Workup

  1. customthe volatiles were removed
  2. customa rotary evaporator
  3. customthe residue purified by silica gel chromatography
  4. wash1:1 CH2Cl2/hexane-CH2Cl2 eluted 4.5 g of methyl 2,6-diacetoxybenzoate

Sources & evidence

ORD record
ord-7485abdbc92c46b59e8053fe3affcf06
Source dataset
uspto-grants-2003_04
Patent number
US06555519B2

Reaction notes

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