Salicylic Acid → Benzyl Salicylate

HRID 1259016

Reaction equation

HRID 1259016 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7]Br)=[CH:3][CH:2]=1.[C:9]([OH:18])(=[O:17])[C:10]1[C:11](=[CH:13][CH:14]=[CH:15][CH:16]=1)[OH:12].O>CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[OH:12][C:11]1[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=1[C:9]([O:18][CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)=[O:17]

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 962WaterHCID 7498Benzyl Bromide

Product 1

HCID 8363Benzyl SalicylateYield 76%

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

BnBr (1.75 mL, 14.631 mmol) was added to a solution of salicylic acid (2.0 g, 14.625 mmol) in TBAF (17.5 mL, 1 M solution in THF) and the reaction mixture was stirred at r.t. overnight (16 h). The organic layer was poured into H2O (100 mL) and extracted with EtOAc (70 mL). It was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (2% EtOAc/hexanes) to furnish 2.53 g of benzyl 2-hydroxybenzoate (colourless oil, yield: 76%).

Workup

  1. extractionextracted with EtOAc (70 mL)
  2. dry with materialIt was dried over Na2SO4 (anhydrous)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on SiO2 (2% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0f302b53436d46b8bb7f6b02c2d94567
Source dataset
uspto-grants-2013_06
Patent number
US08466197B2

Linked notes

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