4-Hydroxybenzaldehyde → Tert-butyl 2-(4-formylphenoxy)acetate

HRID 353188Notes

Reaction equation

HRID 353188 reaction equation
CC(C)([O-])C.[K+].Br[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[OH:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.O>O1CCOCC1>[CH:21]([C:20]1[CH:23]=[CH:24][C:17]([O:16][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:18][CH:19]=1)=[O:22]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 79177tert-Butyl bromoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 639902Tert-butyl 2-(4-formylphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

At room temperature, 31.60 g (281.48 mmol) of potassium tert-butoxide and 52.70 g (270.22 mmol) of tert-butyl bromoacetate are added to a solution of 27.50 g (225.18 mmol) of 4-hydroxybenzaldehyde in 200 ml of dioxane, and the mixture is heated at the boil overnight. 1 l of water is added, and the mixture is then extracted with diethyl ether, washed with 1 N sodium hydroxide solution, water and saturated sodium chloride solution and dried over magnesium sulphate, and the solvent is distilled off. Flash chromatography on silica gel (cyclohexane→cyclohexane/ethyl acetate 20:1→10:1→5:1) gives, after recrystallization from pentane, the target compound.

Workup

  1. temperaturethe mixture is heated at the boil overnight
  2. extractionthe mixture is then extracted with diethyl ether
  3. washwashed with 1 N sodium hydroxide solution, water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. distillationthe solvent is distilled off
  6. customFlash chromatography on silica gel (cyclohexane→cyclohexane/ethyl acetate 20:1→10:1→5:1) gives
  7. customafter recrystallization from pentane

Sources & evidence

ORD record
ord-1bf31d3027f3447fbfed9be119745728
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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