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

HRID 1891433Notes

Reaction equation

HRID 1891433 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17]Br)=[CH:13][CH:12]=1.C([O-])(O)=O.[Na+]>CC#N>[CH2:17]([O:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

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

Product 1

HCID 5612354-Benzyloxy-2-hydroxybenzaldehydeYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the 2,4-dihydroxybenzaldehyde (100 g, 0.67 mol) in CH3CN (1 L), BnBr (112.4 g, 0.67 mol) and NaHCO3 (90.8 g, 0.67 mol) were added. The reaction mixture was refluxed for 48 h and was monitored by TLC. Upon completion, the white precipitate was filtered and the filtrate was evaporated under vacuum. The residue was dissolved in MeOH (500 mL) and was precipitated at 0° C. The precipitates were further recrystallized from MeOH to obtain 4-Benzyloxy-2-hydroxybenzaldehyde (G3a) (127.5 g, 0.56 mol, 84%) as an off-white solid: mp 80-82C (Lit.10 78-80° C.); 1H NMR (DMSO, 400 MHz) δ 10.99 (1H, s), 9.99 (1H, s), 7.37 (5H, m), 6.61 (1H, m), 6.54 (1H, d), 5.15 (2H, s).

Workup

  1. temperatureThe reaction mixture was refluxed for 48 h
  2. filtrationUpon completion, the white precipitate was filtered
  3. customthe filtrate was evaporated under vacuum
  4. dissolutionThe residue was dissolved in MeOH (500 mL)
  5. customwas precipitated at 0° C
  6. customThe precipitates were further recrystallized from MeOH

Sources & evidence

ORD record
ord-0a6367797b9c42b987cdd178578bda17
Source dataset
uspto-grants-2013_08
Patent number
US08507549B2

Reaction notes

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