Methanol → Methyl 5-hydroxy-2-methylbenzoate

HRID 899248Notes

Reaction equation

HRID 899248 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 washed with water and brine, dried over magnesium sulfate, and evaporated. 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 washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel (40 g)
  5. washeluting with hexane/ethyl acetate (10/1)

Sources & evidence

ORD record
ord-4ebdf665f54646c2a496539201e23c85
Source dataset
uspto-grants-2008_04
Patent number
US07354925B2

Reaction notes

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