Methanol → Methyl 3,4-Dihydroxy-2-methylbenzoate

HRID 403172Notes

Reaction equation

HRID 403172 reaction equation
[OH:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([OH:11])=[C:2]([OH:1])[C:3]=1[CH3:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 104420733,4-Dihydroxy-2-methylbenzoic acid

Product 1

HCID 59016598Methyl 3,4-Dihydroxy-2-methylbenzoateYield 83%

Procedure

To a round bottom flask equipped with magnetic stirring and a reflux condenser was added 3,4-dihydroxy-2-methylbenzoic acid (23.3 g, 139 mmol), methanol (139 mL), and concentrated sulfuric acid (0.77 mL, 13.9 mmol). This mixture was heated to reflux for 18 hours. The reaction was cooled to room temperature and the methanol evaporated. The residue was taken up in ether and washed once with saturated sodium bicarbonate solution, once with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated to give a brown solid, methyl-3,4-dihydroxy-2-methylbenzoate, (20.9 g, 114 mmol) in 83% yield. 1H-NMR (300 MHz, CD3COCD3) δ (ppm): 2.47 (s, 3H), 3.79 (s, 3H), 6.78 (d, 1H), 7.46 (d, 1H); TLC: Rf=0.54 (1:1 ethyl acetate/hexane).

Workup

  1. customTo a round bottom flask equipped
  2. temperatureThis mixture was heated
  3. temperatureto reflux for 18 hours
  4. customthe methanol evaporated
  5. washwashed once with saturated sodium bicarbonate solution, once with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-63bb088293dc4ba796584500a35ecbec
Source dataset
uspto-grants-2014_06
Patent number
US08748125B2

Reaction notes

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