Lactic Acid → HCID 13644708, compound
Reaction equation
CN(C1CCCCC1)C.[C:10]([OH:15])(=[O:14])[CH:11]([CH3:13])[OH:12].Cl[CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19].S(=O)(=O)(O)O>>[CH3:17][Si:18]([CH2:21][O:14][C:10](=[O:15])[CH:11]([OH:12])[CH3:13])([CH3:20])[CH3:19]Participants
Procedure
400 g (3.15 moles) of N,N-dimethylcyclohexylamine were dropped into a mixture of 270 g (3 moles) of the S-enantiomer of the lactic acid and 736 g (6 moles) of chloromethyl-trimethyl silane within one hour, whilst stirring at room temperature without external cooling. The reaction mixture was heated to 95° C. with stirring and was kept at this temperature for 12 hours. Then the reaction mixture was cooled to room temperature and was poured into 1.2 liters of 10%-ic aqueous sulphuric acid. The organic phase was separated, washed twice with, in each case, 500 ml of water and was subjected to a fractionated distillation under reduced pressure. 430 g of a distillate were obtained thereby in a first fraction (boiling point: 50° C./20 mbar), which consisted of 15 g of an aqueous phase and of 415 g (3.38 moles) of chloromethyl-trimethylsilane. 371 g (2.10 moles) of the S-enantiomer of the 2-hydroxypropionic acid (trimethylsilyl)-methylester of a purity of 99.5% were obtained in a second fraction at a boiling point of b.p.=40° C./0.1 mbar. Based on chloromethyl-trimethyl-silane which had reacted, a yield of 85.1% of theory was calculated from this.
Workup
- temperatureThe reaction mixture was heated to 95° C.
- stirringwith stirring
- temperatureThen the reaction mixture was cooled to room temperature
- customThe organic phase was separated
- washwashed twice with, in each case, 500 ml of water
- distillationwas subjected to a fractionated distillation under reduced pressure
- custom430 g of a distillate were obtained
Sources & evidence
- ORD record
- ord-b406dbefccea41b7a345fe1c14a481af
- Source dataset
- uspto-grants-1986_02
- Patent number
- US04568760
Reaction notes
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