Sodium Benzoate → HCID 12914085, compound

HRID 1857059Notes

Reaction equation

HRID 1857059 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].Cl[CH2:12][C@H:13]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]1>CN(C)C=O>[C:1]([O:9][CH2:12][C@H:13]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 517055Sodium BenzoateHCID 2734443(R)-(+)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 12914085HCID 12914085, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Sodium benzoate (40.64 g, 0.282 mol) was added to a mixture of (R)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane (42.38 g, 0.282 mol) prepared by the same manner as example 3 and N,N-dimethylformamide (400 ml) and the resulting mixture was stirred for 3 days at 150° C. After cooling the salt was filtered off and N,N-dimethylformamide was removed in vacuo and water was added to the residue and extracted with toluene. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and condensed in vacuo to give 58.63 g of crude (R)-4-benzoyloxymethyl-2,2-dimethyl-1,3-dioxolane (yield 88%).

Workup

  1. temperatureAfter cooling the salt
  2. filtrationwas filtered off
  3. customN,N-dimethylformamide was removed in vacuo and water
  4. additionwas added to the residue
  5. extractionextracted with toluene
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate and condensed in vacuo

Sources & evidence

ORD record
ord-59427592d0c649be8f8f534be510cbc1
Source dataset
uspto-grants-2000_11
Patent number
US06143908

Reaction notes

Loading…