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

HRID 1044442Notes

Reaction equation

HRID 1044442 reaction equation
C(=O)(O)[O-].[Na+].[OH:6][C:7]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[CH2:16]([O:15][C:13]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[C:7]([OH:6])[CH:14]=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 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Anhydrous sodium bicarbonate (0.1 g, 1.2 mmol) was added to a solution of 2,4-dihydroxy-benzaldehyde (0.138 g, 1 mmol) in 10 mL of acetonitrile and the mixture was stirred for 1 hour at RT. Benzylbromide (0.13 mL, 1.1 mmol) was added and the mixture was refluxed for 6 hours. After disappearance of the reactant (TLC), the reaction was poured into ice water with vigorous stirring. A white solid precipitated and it was recrystallized from methanol (ca. 4 mL) to obtain 0.182 g (80%) of white powder: mp 78-80° C.; TLC Rf0.88 in toluene:methanol (10:1); 1H NMR (600 MHz, acetone-d6) δ 11.41 (s, 1H, OH), 9.81 (s, 1H, CHO), 7.68-7.67 (d, 1H, J=8.4 Hz, Ar—H6), 7.45-7.35 (m, 5H, C6H5), 6.71-6.69 (dd, 1H, 2J=8.4 Hz, 3J=2.4 Hz, Ar—H5), 6.56 (d, 1H, J=1.8 Hz, Ar—H3), 5.24 (s, 2H, PhCH2); 13C NMR (100 MHz, acetone-d6) 194.61, 166.1, 164.4, 135.9, 128.9, 128.6, 127.8, 115.5, 109.1, 101.8, 70.6; analysis calcd. for C14H12O3: C, 73.67; H, 5.30. found: C, 73.62; H, 5.35.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customA white solid precipitated
  3. customit was recrystallized from methanol (ca. 4 mL)

Sources & evidence

ORD record
ord-9b1f6841e2774e13afa1d3e73059f494
Source dataset
uspto-grants-2013_10
Patent number
US08563599B2

Reaction notes

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