3-Hydroxy-4-methylbenzoic acid → Methyl 3-hydroxy-4-methylbenzoate

HRID 417070Notes

Reaction equation

HRID 417070 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[C:12](=O)(O)[O-].[Na+]>Cl>[CH3:12][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([OH:1])[CH:3]=1

Participants

4

Reactant 2

HCID 685123-Hydroxy-4-methylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 354091Methyl 3-hydroxy-4-methylbenzoateYield 99%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The solution of 3-hydroxy-4-methylbenzoic acid (commercially available) in 32 mL hydrochloric acid (1.25M in methanol) was refluxed for 5 h. After cooling to room temperature the solution was poured on saturated aqueous sodium bicarbonate solution and extracted three times with ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate and filtered to give the product as a white solid (99%) which was pure enough for the next step. MS (Turbo Spray): m/z=165.1 [M−H].

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-46661021f9de4fb7825af8c1f83377d7
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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