Mandelic Acid → HCID 12440727, compound

HRID 267496Notes

Reaction equation

HRID 267496 reaction equation
[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[C:12](=[S:14])=[S:13].[OH-].[K+].[CH3:17]I>CS(C)=O>[CH3:17][S:13][C:12](=[S:14])[O:3][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 1292Mandelic AcidHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 14797Potassium Hydroxide

Product 1

HCID 12440727HCID 12440727, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.56 g (30 mM) of DL-mandelic acid are dissolved in 100 ml. of carbon disulfide and 3.37 g. (60 mM) of pulverized potassium hydroxide are added all at once. Absolute dimethylsulfoxide is then added with stirring until a clear solution is obtained. The whole is stirred for 1 hour and then 4.26 g (30 mM) of methyl iodide are added. After 4 hours the carbon disulfide is removed in vacuum and the oily residue is dissolved in 200 ml. of water. The aqueous solution is extracted three times with 50 ml. of ether. After cooling the aqueous phase to 5°, it is acidified with 2N hydrochloric acid and extracted with ether. From the ether, 3.1 g. of crude DL-α-[(methylthio)thioxomethoxy]benzene acetic acid is obtained. Recrystallization from benzol/cyclohexane yields 2.7 g., m.p. 109°-110°.

Workup

  1. customis obtained
  2. stirringThe whole is stirred for 1 hour
  3. customAfter 4 hours the carbon disulfide is removed in vacuum
  4. dissolutionthe oily residue is dissolved in 200 ml
  5. extractionThe aqueous solution is extracted three times with 50 ml
  6. temperatureAfter cooling the aqueous phase to 5°
  7. extractionextracted with ether

Sources & evidence

ORD record
ord-deb42e8ba60848b3966bb011d9d61336
Source dataset
uspto-grants-1976_03
Patent number
US03943130

Reaction notes

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