4-Hydroxybenzaldehyde → Ethyl 2-(4-formylphenoxy)-2-methylpropanoate

HRID 1295094Notes

Reaction equation

HRID 1295094 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[C:17]([CH3:24])([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19].O>CC(C)=O>[CH2:21]([O:20][C:18](=[O:19])[C:17]([CH3:24])([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium Carbonate2×HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester2×

Product 1

HCID 13134808Ethyl 2-(4-formylphenoxy)-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 4-hydroxybenzaldehyde (20 g, 0.164 mol) in acetone (300 mL) was added K2CO3 (34 g, 1.5 equiv.) and the reaction was stirred at room temperature during 30 minutes. Ethyl 2-bromo-2-methylpropionate (36.2 mL, 1.5 equiv.) was added dropwise and the mixture was heated under reflux during 3 hours. K2CO3 (34 g, 1.5 equiv.) and ethyl 2-bromo-2-methylpropionate (36.2 mL, 1.5 equiv.) were added and the mixture was heated under reflux during 16 hours and then pourred into water and extracted with CH2Cl2 (3×300 mL). The combined organic layers were dried over Na2SO4, filtered and the solvent evaporated to afford crude intermediate. After chromatography on silicagel, eluting with cyclohexane/CH2Cl2 (6/4, then 8/2) and then with CH2Cl2, the titled compound was obtained as an oil (27 g, 69.85%)

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux during 3 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux during 16 hours
  5. extractionextracted with CH2Cl2 (3×300 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customto afford crude intermediate
  10. washAfter chromatography on silicagel, eluting with cyclohexane/CH2Cl2 (6/4

Sources & evidence

ORD record
ord-3d53c01b911442af836b89f1d30140ed
Source dataset
uspto-grants-2007_07
Patent number
US07241793B2

Reaction notes

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