Salicylaldehyde → HCID 11447699, compound
Reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7](=[O:15])[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10].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:10][C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[CH:7]=[O:15])=[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 salicylaldehyde. 181.2 g (1.2 mol) of t-butyl chloroacetate were added dropwise to the mixture at a temperature of 50° C. for three hours. After the addition, the mixture was stirred for three hours at a temperature of 50° C. The resulting reaction mixture was washed with 122 g of toluene and 662 g of water. 130 g of the solvent was removed from the mixture by distillation and then 122 g of n-heptane were added to the distillation residue to effect crystallization. The resulting crystals were collected by filtration to provide 122.3 g of 2-t-butoxycarbonylmethoxybenzaldehyde having a purity of 98.5% as brown or pale yellow crystals. The filtrate was concentrated and provided 52.6 g of 2-t-butoxycarbonylmethoxybenzaldehyde having a purity of 98.0%. FIG. 1 is an infrared absorption spectrum of the compound. The overall yield was 74%.
Workup
- additionAfter the addition
- customThe resulting reaction mixture
- washwas washed with 122 g of toluene and 662 g of water
- custom130 g of the solvent was removed from the mixture by distillation
- addition122 g of n-heptane were added to the distillation residue
- customcrystallization
- filtrationThe resulting crystals were collected by filtration
Sources & evidence
- ORD record
- ord-889156c5c68c4df58b6040aa72950840
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06603029B1
Reaction notes
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