4-Methyloxybenzyl chloride → HCID 11095877, compound
Reaction equation
[OH:1][C@@H:2]([CH3:6])[C:3]([OH:5])=[O:4].CC(C)([O-])C.[K+].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1>CN(C=O)C>[OH:1][C@@H:2]([CH3:6])[C:3]([O:5][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1)=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a stirred solution of (S)(+)-2 hydroxypropionic acid (9.0 g, 100 mmole) in 100 ml dry DMF was added potassium tert-butoxide (12.34 g, 110 mmole) and the mixture was stirred for one hour at 25° C. 4Methoxybenzyl chloride (18.8 g 120 mmole) was added and the mixture was stirred for six hours at 60° C. The mixture was evaporated under reduced pressure and 250 ml ethyl acatate was added. The organic phase was washed four times with water. The organic phase was dried with sodium sulfate and concentrated in vacuo. Yield: 15.6 g=74%
Workup
- stirringthe mixture was stirred for six hours at 60° C
- customThe mixture was evaporated under reduced pressure and 250 ml ethyl acatate
- additionwas added
- washThe organic phase was washed four times with water
- dry with materialThe organic phase was dried with sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-19c413e113a94f7bb5c0181f0e129f86
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06458772B1
Reaction notes
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