Lactic Acid → HCID 54500398, compound

HRID 1065528Notes

Reaction equation

HRID 1065528 reaction equation
C(Br)(C)(C)C.[C:6]([OH:11])(=[O:10])[CH:7]([CH3:9])[OH:8].C(=O)(O)[O-].[Na+].O.[CH3:18][S:19]([CH3:21])=O>>[CH3:18][S:19][CH2:21][O:10][C:6](=[O:11])[CH:7]([CH3:9])[OH:8]

Participants

6

Reactant 5

HCID 612Lactic AcidHCID 679Dimethyl SulfoxideHCID 962WaterHCID 10485t-Butyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 54500398HCID 54500398, compound

Procedure

153 ml (1.1 mol) of tert.butyl bromide are slowly added dropwise to a suspension of 10 g (0.11 mol) of L (+)-lactic acid and 94.2 g (1.1 mol) of sodium bicarbonate in 200 ml of dimethyl sulphoxide. The mixture is stirred for 48 hours, then poured into 1 liter of water and extracted twice with 100 ml of ethyl acetate each time. The organic phase is back-washed three times with 200 ml of water each time and subsequently evaporated. The crude product is chromatographed on a 20-fold amount of silica gel with n-hexane/ethyl acetate (4:1) and the eluate is evaporated. There are obtained 5.7 g of L (-)-lactic acid [(methylthio)methyl] ester; [α]D20 =-39.27° (c=1.3% in chloroform).

Workup

  1. extractionextracted twice with 100 ml of ethyl acetate each time
  2. washThe organic phase is back-washed three times with 200 ml of water each time
  3. customsubsequently evaporated
  4. customThe crude product is chromatographed on a 20-fold amount of silica gel with n-hexane/ethyl acetate (4:1)
  5. customthe eluate is evaporated

Sources & evidence

ORD record
ord-dcdef395a9fd4c43981114255cf0a5d6
Source dataset
uspto-grants-1982_05
Patent number
US04329488

Reaction notes

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