Vanillin → 4-[(4-Chlorophenyl)methoxy]-3-methoxybenzaldehyde

HRID 1261040Notes

Reaction equation

HRID 1261040 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=2[O:10][CH3:11])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzene

Product 1

HCID 7182634-[(4-Chlorophenyl)methoxy]-3-methoxybenzaldehydeYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 4-hydroxy-3-methoxybenzaldehyde (105, 600.0 mg, 3.94 mmol) and 4-chlorobenzyl bromide (557, 1.20 g, 5.84 mmol) in acetonitrile (6 mL) was added potassium carbonate (0.390 g, 2.82 mmol). The reaction was microwaved on 300 watts, 120° C. for 10 minutes. The reaction was extracted with ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, filtered and the volatiles removed by evaporation. The desired compound was purified by recrystallization from hexanes to provide 106 (1.01 g, 93%). MS (ESI) [M−H+]−=275.1.

Workup

  1. customThe reaction was microwaved on 300 watts, 120° C. for 10 minutes
  2. extractionThe reaction was extracted with ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe volatiles removed by evaporation
  7. customThe desired compound was purified by recrystallization from hexanes

Sources & evidence

ORD record
ord-4df51388b0414302b5d69d55c127c094
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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