Methanol → 3-Benzyloxybenzaldehyde

HRID 25834

Reaction equation

HRID 25834 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].C[OH:22].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)(Cl)Cl>[CH2:23]([O:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH:1]=[O:22])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1408973-Benzylphenol

Product 1

HCID 743423-Benzyloxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-hydroxylbenzaldehyde 31 (5.0 g, 40 mmol) and K2CO3 (27.2 g, 197 mmol) in 200 ml CHCl3: 100 ml MeOH was added benzylbromide (5.9 ml, 49 mmol). The suspension was refluxed under nitrogen overnight. The solvent was removed by evaporation and the resulting oil was taken up in DCM and washed with water and brine and dried (Na2SO4). The crude product was purified by column chromatography to yield the product as a viscous oil which solidified upon sitting (8.48 g, 40 mmol, 98%). m.p. 46°. 1H NMR (500 MHz, CDCl3) δ 9.97 (s, 1H), 7.48-7.25 (m, 9H), 5.13 (s, 2H). 13C NMR (125 MHz, CD3OD) δ 191.8, 159.2, 137.8, 136.3, 130.0, 128.6, 128.1, 127.5, 123.41, 121.9, 113.3, 70.0. HRMS (EI) m/e calcd for C14H12O2: 212.08373, found: 212.0827.

Workup

  1. temperatureThe suspension was refluxed under nitrogen overnight
  2. customThe solvent was removed by evaporation
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-56afacbd8edf4ddb94d3f3ca93a30eb6
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Linked notes

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