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

HRID 1891428Notes

Reaction equation

HRID 1891428 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.C1(C)C=CC=CC=1.CO>[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

6

Reactant 3

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

Product 1

HCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21867641Toluene methanolSolvent

Procedure

Anhydrous sodium bicarbonate (1 g, 12 mmol) was added to a solution of 2,4-dihydroxybenzaldehyde (1.38 g, 10 mmol) in 50 mL of acetonitrile and the mixture was stirred for 1 hour at RT. Benzylbromide (1.2 mL, 10 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. 40 mL) to obtain (1.82 g, 80 of P1 as a white powder: mp 78-80° C.; TLC Rf 0.88 in toluene:methanol (10:1); 1H NMR (600 MHz, acetone-d6) δ 11.41 (s, 1H, OH), 9.81 (s, 1H, CHO), 7.67 (d, 1H, J=8.4 Hz, Ar—H6), 7.45-7.35 (m, 5H, C6H5), 6.70 (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).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customA white solid precipitated
  3. customit was recrystallized from methanol (ca. 40 mL)
  4. customto obtain (1.82 g, 80 of P1 as a white powder

Sources & evidence

ORD record
ord-e17d6fb5d1664071be3a38adbaf2db2d
Source dataset
uspto-grants-2013_08
Patent number
US08507549B2

Reaction notes

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