Sulfuric acid magnesium salt (1:1) → Benzoic acid, 3,5-dimethyl-, methyl ester

HRID 2289112Notes

Reaction equation

HRID 2289112 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:12])[C:10]=1O)[C:5]([OH:7])=[O:6].[CH3:13][Si](C=[N+]=[N-])(C)C.S([O-])([O-])(=O)=O.[Mg+2]>CCOCC.CO>[CH3:13][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([CH3:1])[CH:10]=[C:9]([CH3:12])[CH:8]=1

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 1383874-Hydroxy-3,5-dimethylbenzoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 32786Benzoic acid, 3,5-dimethyl-, methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3,5-dimethyl-4-hydroxybenzoic acid (1.0 g) in ether (5 mL) and methanol(5 mL) was treated with excess trimethylsilyldiazomethane. After stirring 30 min at room temperature the reaction was treated with magnesium sulfate, filtered and concentrated to a brown solid. The title compound was obtained by purification on silica gel to give a colorless solid (670 mg). NMR (CDCl3); δ 7.75 (s,2H), 3.85 (s,3H), 2.30 (s,6H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to a brown solid

Sources & evidence

ORD record
ord-7fa7046de10b4ca9a7dbe4114e60116b
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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