Methanol → 4-Acetoxy-2-methoxy-benzoic acid methyl ester

HRID 1821522Notes

Reaction equation

HRID 1821522 reaction equation
CO.[CH3:3][O:4][C:5](=[O:17])[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13](=[O:15])[CH3:14])=[CH:8][C:7]=1[OH:16].[CH:18]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>ClCCl>[CH3:3][O:4][C:5](=[O:17])[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13](=[O:15])[CH3:14])=[CH:8][C:7]=1[O:16][CH3:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 579902174-Acetoxy-2-hydroxy-benzoic acid methyl ester

Product 1

HCID 534162044-Acetoxy-2-methoxy-benzoic acid methyl esterYield 106.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MeOH (0.3 mL, 7.4 mmol) was added to the product from step 1 (0.962 g, 4.6 mmol), Ph3P (1.79 g, 6.8 mmol), and dichloromethane (10 mL). Then DEAD (1.32 mL, 8.4 mmol) was added to the reaction. Reaction was stirred at room temperature for 4 days. Reaction solution was concentrated by rotary evaporation and the resulting residue was purified with silica gel prep plates and 1:3 EtOAc/Hexane as eluent. Obtained 1.10 g of 4-Acetoxy-2-methoxy-benzoic acid methyl ester in quantitative yield.

Workup

  1. customReaction
  2. customReaction solution
  3. concentrationwas concentrated by rotary evaporation
  4. customthe resulting residue was purified with silica gel prep plates and 1:3 EtOAc/Hexane as eluent

Sources & evidence

ORD record
ord-44376d754dcb4dccb251c22289230b68
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

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