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

HRID 2258018Notes

Reaction equation

HRID 2258018 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]>C(O)C>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][C:17]([CH3:24])([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

Product 1

HCID 13134808Ethyl 2-(4-formylphenoxy)-2-methylpropanoateYield 39.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4Hydroxybenzaldehyde (24.4 g, Aldrich) was dissolved in absolute ethanol (470 ml) and anhy. K2CO3 (27.6 g) and ethyl 2-bromoisobutyrate (39.0 g, Aldrich) added. The resulting mixture was refluxed overnight, allowed to cool and the solvent removed in vacuo. The residue was suspended in water (300 ml) and extracted with CH2Cl2. The combined organic layers were washed with 1.0N aqu. NaOH and water, then dried over MgSO4. Removal of the solvent in vacuo and vacuum distillation of the residue gave the desired product (18.8 g, bp 110°-118° C./0.1 mm Hg).

Workup

  1. temperatureThe resulting mixture was refluxed overnight
  2. temperatureto cool
  3. customthe solvent removed in vacuo
  4. extractionextracted with CH2Cl2
  5. washThe combined organic layers were washed with 1.0N aqu
  6. dry with materialNaOH and water, then dried over MgSO4
  7. customRemoval of the solvent
  8. distillationin vacuo and vacuum distillation of the residue

Sources & evidence

ORD record
ord-b260ca626eb442b791ed1f65529d5116
Source dataset
uspto-grants-1997_08
Patent number
US05658944

Reaction notes

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