4-Hydroxybenzaldehyde → Tert-butyl 2-(4-formylphenoxy)acetate
Reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.Cl[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>CN(C)C=O>[C:21]([O:20][C:18]([CH2:17][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)=[O:19])([CH3:24])([CH3:23])[CH3:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
366 g of dimethylformamide and 165.9 g (1.2 mol) of potassium carbonate were placed in a flask, followed by dropwise addition of 122 g (1 mol) of 4-hydroxybenzaldehyde. 181.2 g (1.2 mol) of t-butyl chloroacetate were added dropwise to the mixture at a temperature of 50° C. for two hours. After the addition, the mixture was stirred for two hours at a temperature of 50° C. and then another seven hours at a temperature of 70° C. The resulting reaction mixture was washed with 122 g of toluene and 662 g of water. 100 g of the solvent was removed from the mixture by distillation under reduced pressure and then 236 g of n-heptane were added to the distillation residue to effect crystallization. The resulting crystals were collected by filtration to provide 128.4 g of 4-t-butoxycarbonylmethoxybenzaldehyde having a purity of 99.9% as white crystals. FIG. 2 is an infrared absorption spectrum of the compound. The yield was 54%.
Workup
- additionAfter the addition
- customanother seven hours
- customat a temperature of 70° C
- customThe resulting reaction mixture
- washwas washed with 122 g of toluene and 662 g of water
- custom100 g of the solvent was removed from the mixture by distillation under reduced pressure
- addition236 g of n-heptane were added to the distillation residue
- customcrystallization
- filtrationThe resulting crystals were collected by filtration
Sources & evidence
- ORD record
- ord-eb02f588d7544c95b1402d8627d1b25f
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06603029B1
Reaction notes
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