N,N-Dimethylaniline → HCID 12438231, compound

HRID 1657375Notes

Reaction equation

HRID 1657375 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].CN(C)C1C=CC=CC=1.Cl[C:22]([O:24][CH3:25])=[O:23]>O1CCCC1>[CH3:25][O:24][C:22]([O:3][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:11])=[O:10])=[O:23]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 1292Mandelic AcidHCID 6586Methyl chloroformate

Product 1

HCID 12438231HCID 12438231, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60 gms. (0.4 moles) of DL-mandelic acid are dissolved in 50 ml. of tetrahydrofuran. 50 gms. (0.4 moles) of dimethylaniline are added and the mixture is cooled to -20°. 45 gms. (0.5 moles) of methyl chloroformate are added with vigorous stirring. After 30 minutes, the reaction mixture is poured into 500 ml. of ice-water and extracted with ethyl acetate. The organic phase is washed with 100 ml. of 2N HCl solution and concentrated after drying over sodium sulfate. A light oil is obtained which crystallizes on standing overnight. The product, DL-α-[(methoxycarbonyl)oxy]-phenylacetic acid is recrystallized from cyclohexane to obtain white crystals, m.p. 103°-105°.

Workup

  1. temperaturethe mixture is cooled to -20°
  2. additionthe reaction mixture is poured into 500 ml
  3. extractionof ice-water and extracted with ethyl acetate
  4. washThe organic phase is washed with 100 ml
  5. concentrationof 2N HCl solution and concentrated
  6. dry with materialafter drying over sodium sulfate
  7. customA light oil is obtained which
  8. customcrystallizes
  9. waiton standing overnight
  10. customThe product, DL-α-[(methoxycarbonyl)oxy]-phenylacetic acid is recrystallized from cyclohexane
  11. customto obtain white crystals, m.p. 103°-105°

Sources & evidence

ORD record
ord-ac2c822d6b5c4b6cb13d6a4a9bc6e186
Source dataset
uspto-grants-1976_06
Patent number
US03960850

Reaction notes

Loading…