4-Hydroxybenzaldehyde → tert-Butyl 2-(4-formylphenoxy)-2-methylpropanoate

HRID 353189Notes

Reaction equation

HRID 353189 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]([CH3:26])([CH3:25])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].O>CN(C)C=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][C:17]([CH3:26])([CH3:25])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium Carbonate2×HCID 90290tert-Butyl 2-bromo-2-methylpropionate2×

Product 1

HCID 22708193tert-Butyl 2-(4-formylphenoxy)-2-methylpropanoateYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

24.42 g (200 mmol) of 4-hydroxybenzaldehyde are dissolved in 250 ml of N,N-dimethylformamide and treated with 27.64 g (200 mmol) of potassium carbonate. At 100° C., 53.55 g (240 mmol) of tert-butyl α-bromoisobutyrate are added dropwise. The mixture is stirred for another hour, a further 200 mmol of potassium carbonate and 240 mmol of tert-butyl α-bromoisobutyrate are added and, after 4 hours at 100° C., 1 l of water is added. Following extraction with diethyl ether, washing with 1 N aqeuous sodium hydroxide solution and saturated sodium chloride solution and drying over magnesium sulphate, the solvent is distilled off and the residue is purified by flash chromatography on silica gel (cyclohexane→cyclohexane/ethyl acetate 20:1→10:1→5:1) and dried under reduced pressure. The target compound is obtained in the form of colourless crystals in a yield of 42%.

Workup

  1. extractionextraction with diethyl ether
  2. washwashing with 1 N aqeuous sodium hydroxide solution and saturated sodium chloride solution
  3. dry with materialdrying over magnesium sulphate
  4. distillationthe solvent is distilled off
  5. customthe residue is purified by flash chromatography on silica gel (cyclohexane→cyclohexane/ethyl acetate 20:1→10:1→5:1)
  6. customdried under reduced pressure
  7. customThe target compound is obtained in the form of colourless crystals in a yield of 42%

Sources & evidence

ORD record
ord-361f1f9950734d1f826f3bc63a7e063d
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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