Water → 2-(Benzyloxy)-3-methoxybenzaldehyde

HRID 413789

Reaction equation

HRID 413789 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:13]([CH:14]=[O:15])[C:12]=1[OH:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[I-].[K+]>[CH2:1]([O:19][C:12]1[C:11]([O:10][CH3:9])=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8991o-VanillinHCID 11430Potassium Carbonate

Product 1

HCID 12680872-(Benzyloxy)-3-methoxybenzaldehydeYield 81%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Benzyl bromide (8.6 ml) was added to a stirred solution of 3-methoxysalicylaldehyde (10 g), potassium carbonate (14.76 g) and potassium iodide (0.12 g) in DMF (120 ml) under an atmosphere of argon. The reaction was heated at 70° C. for 16 hours. Water (200 ml) was added causing the precipitation of a brown oil which crystallised on cooling. The solid was filtered, washed with water, dissolved in dichloromethane and dried (MgSO4). The solvent was removed in vacuo to give an oil which crystallised on trituration with iso-hexane to give the product as an off white solid (12.85 g, 81%); NMR d (CD3SOCD3) 3.91 (s, 3H), 5.15 (s, 2H), 7.14-7.22 (m, 2H), 7.29-7.42 (m, 6H), 10.10 (t, 1H); M/z (+) 243 (MH+).

Workup

  1. customthe precipitation of a brown oil which
  2. customcrystallised
  3. temperatureon cooling
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. dissolutiondissolved in dichloromethane
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed in vacuo
  9. customto give an oil which
  10. customcrystallised on trituration with iso-hexane

Sources & evidence

ORD record
ord-85cf6ef0ec784178b2581fde72b3ab84
Source dataset
uspto-grants-2003_05
Patent number
US06569888B1

Linked notes

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