Benzyl Bromide → 5-(Benzyloxy)-2-methoxybenzaldehyde

HRID 922398Notes

Reaction equation

HRID 922398 reaction equation
C[O-].[Na+].[C:4](=O)(OC)[O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([CH:14]=[O:15])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH:25]1[CH:30]=[CH:29][C:28](CBr)=[CH:27][CH:26]=1>CO.O>[CH2:4]([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([CH:7]=1)[CH:14]=[O:15])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10942334Sodium MethoxideHCID 156364273-Formyl-4-methoxyphenyl methyl carbonate

Product 1

HCID 109666945-(Benzyloxy)-2-methoxybenzaldehydeYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of sodium methoxide (257 mg. 4.8 mmol) in MeOH (20 mL) at room temperature was added 3-formyl-4-methoxyphenyl methyl carbonate (6, 1.0 g, 4.8 mmol). The resulting orange solution was stirred for 45 min and concentrated to dryness. The residue was dissolved in DMF (2 mL) and treated with K2CO3 (1.3 g, 9.4 mmol) and BnBr (0.57 mL, 4.8 mL). The reaction mixture was stirred for 15 h and it was poured into water (20 mL). The precipitate was collected, washed with water and dried in vacuo to afford the title compound (1.13 g, 98%) as a light yellow solid: 1H NMR (500 MHz, CDCl3) δ 10.44 (s, 1H), 7.49-7.41 (m, 3H), 7.40-7.36 (m, 2H), 7.35-7.30 (m, 1H), 7.21 (dd, J=9.1, 3.2 Hz, 1H), 6.95 (d, J=9.1 Hz, 1H), 5.05 (s, 2H), 3.90 (s, 3H); ESI MS m/z 243 [M+H]+.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in DMF (2 mL)
  3. stirringThe reaction mixture was stirred for 15 h
  4. customThe precipitate was collected
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-8a754f9a14514befa538fb6fe38d567d
Source dataset
uspto-grants-2016_03
Patent number
US09278940B2

Reaction notes

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