Potassium Hydroxide → 3-Benzyl-2-hydroxybenzoic acid

HRID 2100296Notes

Reaction equation

HRID 2100296 reaction equation
[C:1]1([CH2:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:10]([CH:11]=[O:12])[C:9]=2[OH:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:17].[K+]>C(O)C.O.[N+]([O-])([O-])=O.[Ag+]>[C:1]1([CH2:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:10]([C:11]([OH:17])=[O:12])[C:9]=2[OH:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 222635343-(Phenylmethyl)salicylaldehyde

Product 1

HCID 139224293-Benzyl-2-hydroxybenzoic acidYield 34.3%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

According to the general method of Sharma et al., 2000, Synth. Commun., 30:397-405, a stirred solution of the 3-(phenylmethyl)salicylaldehyde (1.27 g, 6 mmol) in ethanol (16 ml) was treated dropwise with a solution of silver nitrate (2.0 g, 12 mmol) in water (16 ml). A solution of potassium hydroxide (2.69 g, 48 mmol) was then added dropwise over 40 minutes. The solution was allowed to stir at RT for 6 h. The mixture was filtered through a pad of celite, and the filter pad washed with water (2×10 ml). The filtrate was washed with diethyl ether (2×15 ml) and then acidified with 1N HCl. The milky suspension was extracted with diethyl ether (2×30 ml), and the combined extracts were dried (Na2SO4) and the solvent removed to yield 3-(phenylmethyl)salicylic acid as a tan solid (0.47 g, 34%). 1H-NMR (CDCl3, 400 MHz): δ 4.02 (s, 2H), 6.84 (t, 1H, J=8 Hz), 7.19-7.32 (m, 6H), 7.79 (d, 1H, J=8 Hz), 10.74 (s, 1H).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washthe filter pad washed with water (2×10 ml)
  3. washThe filtrate was washed with diethyl ether (2×15 ml)
  4. extractionThe milky suspension was extracted with diethyl ether (2×30 ml)
  5. dry with materialthe combined extracts were dried (Na2SO4)
  6. customthe solvent removed

Sources & evidence

ORD record
ord-179bc502cae443a2bc8b993eca48d493
Source dataset
uspto-grants-2009_08
Patent number
US07572791B2

Reaction notes

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