Methanol → Methyl 2-hydroxy-3-benzylbenzoate

HRID 2100297Notes

Reaction equation

HRID 2100297 reaction equation
S(=O)(=O)(O)O.[C:6]1([CH2:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:15]([C:16]([OH:18])=[O:17])[C:14]=2[OH:22])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:23]O>>[C:6]1([CH2:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:15]([C:16]([O:18][CH3:23])=[O:17])[C:14]=2[OH:22])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 139224293-Benzyl-2-hydroxybenzoic acid

Product 1

HCID 22263561Methyl 2-hydroxy-3-benzylbenzoateYield 46%

Procedure

To a solution of the acid (0.47 g, 2.1 mmol) in dry methanol (40 ml) was added conc. Sulfuric acid (0.47 g) and the solution heated to reflux for 96 h. Upon cooling the methanol was removed and the residue taken up in water (50 ml), and extracted with dichloromethane (3×30 ml). The combined extracts were dried (Na2SO4), and the solvent removed. The residue was eluted through a silica column using 5% ethyl acetate in petroleum spirit to yield a colorless oil (0.23 g, 46%). 1H-NMR (CDCl3, 300 MHz): δ 3.94 (s, 3H), 4.03 (s, 2H), 6.81 (t, 1H, J=8 Hz), 7.20-7.32 (m, 6H), 7.73 (dd 1H, J=8 Hz, 1.5 Hz), 11.10 (s, 1H).

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 96 h
  3. customwas removed
  4. extractionextracted with dichloromethane (3×30 ml)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customthe solvent removed
  7. washThe residue was eluted through a silica column

Sources & evidence

ORD record
ord-3da53da24ed444818f109f6802778ea0
Source dataset
uspto-grants-2009_08
Patent number
US07572791B2

Reaction notes

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