Methanol → Methyl 5-hydroxy-2-methylbenzoate

HRID 1179276Notes

Reaction equation

HRID 1179276 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].CO.[CH3:14][Si](C=[N+]=[N-])(C)C.C(OCC)C>ClCCl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:14])=[O:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 2351885-Hydroxy-2-methylbenzoic acid

Product 1

HCID 13929055Methyl 5-hydroxy-2-methylbenzoateYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5-hydroxy-2-methylbenzoic acid (WO 9619437, 1.11 g, 6.69 mmol), in dichloromethane (6 mL) and methanol (6 mL) was added a 2.0 M solution of (trimethylsilyl)diazomethane in diethyl ether (7.31 mL, 14.7 mmol) at 0° C. The mixture was stirred at room temperature for 3 days, and the mixture was diluted with dichloromethane (200 mL). The solution was washed with water and brine, dried over magnesium sulfate, and evapolated. The residue was purified by column chromatography on silica gel (40 g) eluting with hexane/ethyl acetate (10/1) to afford 545 mg (49%) of the title compound:

Workup

  1. washThe solution was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe residue was purified by column chromatography on silica gel (40 g)
  4. washeluting with hexane/ethyl acetate (10/1)

Sources & evidence

ORD record
ord-53e896984ee343f581210849504f486d
Source dataset
uspto-grants-2007_10
Patent number
US07279486B2

Reaction notes

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