Syringaldehyde → 4-(4-Isopropylbenzyloxy)-3,5-dimethoxybenzaldehyde

HRID 1166776Notes

Reaction equation

HRID 1166776 reaction equation
[CH:1](=[O:13])[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[CH:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1)([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21][O:8][C:7]2[C:9]([O:10][CH3:11])=[CH:12][C:2]([CH:1]=[O:13])=[CH:3][C:4]=2[O:5][CH3:6])=[CH:19][CH:18]=1)([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8655SyringaldehydeHCID 11430Potassium CarbonateHCID 749164-Isopropylbenzyl chloride

Product 1

HCID 229993894-(4-Isopropylbenzyloxy)-3,5-dimethoxybenzaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Syringaldehyde (4-hydroxy-3,5-dimethoxybenzaldehyde) (10.2 g, 55 mmol) was dissolved in DMF (45 ml), and 4-isopropylbenzylchloride (9.7 g, 55 mmol) and potassium carbonate (11.5 g) were added successively. The resulting mixture was heated at 60° C. for 16 hours. After cooling, the mixture was partitioned between water (150 ml) and ethyl acetate (3×100 ml). The combined organic extracts were washed with water (100 ml), saturated NaCl (100 ml), dried (MgSO4), treated with activated carbon, filtered and concentrated in vacuo to afford 15 g (100%) of 4-(4-isopropylbenzyloxy)-3,5-dimethoxybenzaldehyde as an oil.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between water (150 ml) and ethyl acetate (3×100 ml)
  3. washThe combined organic extracts were washed with water (100 ml), saturated NaCl (100 ml)
  4. dry with materialdried (MgSO4)
  5. additiontreated with activated carbon
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe2fd680c85849fdae8d7ca575829518
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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