Methanol → Methyl 2-hydroxy-3-benzylbenzoate

HRID 750455Notes

Reaction equation

HRID 750455 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 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-bb0151e98f4f4e9ca6a49734518f3e68
Source dataset
uspto-grants-2008_07
Patent number
US07405211B2

Reaction notes

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