2,4-Dihydroxybenzaldehyde → 4-Benzyloxy-2-hydroxybenzaldehyde

HRID 1891431Notes

Reaction equation

HRID 1891431 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])(O)=O.[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC#N>[CH2:16]([O:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[CH:9]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 7498Benzyl BromideHCID 516892Sodium Bicarbonate

Product 1

HCID 5612354-Benzyloxy-2-hydroxybenzaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,4-dihydroxybenzaldehyde (100 g, 0.72 mol) in CH3CN (1.5 L), NaHCO3 (72.0 g, 0.86 mol) and benzyl bromide (145.4 g, 0.85 mol) were added and the reaction mixture was stirred under reflux. The reaction progression was followed by TLC and on completion the reaction mixture was cooled to room temperature and filtered. The organic solvents were evaporated under vacuum. The off white residue was recrystallized from MeOH to obtain 4-benzyloxy-2-hydroxybenzaldehyde (B2a) (140 g, 0.61 mol) in 85% yield: mp 77-79° C. [lit.42 mp 78-80° C.); TLC Rf 0.73 [EtOAc/hexanes (1:2)]; ((CD3)2CO, 600 MHz) δ 11.50 (1H, s), 9.88 (1H, br), 7.67 (1H, d, J=5.4 Hz), 7.50 (2H, d, J=7.2), 7.41 (2H, m), 7.36 (1H, m), 6.71 (1H, m), 6.57 (1H, s), 5.24 (2H, s).

Workup

  1. temperatureunder reflux
  2. filtrationfiltered
  3. customThe organic solvents were evaporated under vacuum
  4. customThe off white residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-36dd4e9c6fe64355bd16ffe378af1d53
Source dataset
uspto-grants-2013_08
Patent number
US08507549B2

Reaction notes

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