Acetone → 3-(Benzyloxy)-1,2-propanediol

HRID 553264Notes

Reaction equation

HRID 553264 reaction equation
CC(C)=O.[OH:5][CH2:6][CH:7]([CH2:9][OH:10])[OH:8].[OH-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.S(=O)(=O)(O)O.C(N(CC)CC)C>[CH2:13]([O:5][CH2:6][CH:7]([OH:8])[CH2:9][OH:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 180AcetoneHCID 753GlycerolHCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide

Product 1

HCID 980723-(Benzyloxy)-1,2-propanediolYield 84%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

Into a mixed solution of acetone (800 ml) and glycerin (199 g, 2.16 mol) was added 98% sulfuric acid (6.9 g) at about 25° C., and the mixture was stirred for 3 hours. To this reaction solution was added triethylamine (18.0 g), and the solvent was distilled off under reduced pressure. Into a solution prepared by suspending sodium hydroxide (98.5 g) in toluene (526 ml) was dropped the above-described concentration residue at 55 to 75° C. Into this reaction solution, benzyl chloride (229 g, 1.81 mol) was dropped at 95 to 105%, and the mixture was reacted for 5 hours while distilling components of lower boiling points off. After completion of the reaction, water (366 ml) was added, and the liquid was partitioned. To the resultant toluene layer was added 98% sulfuric acid (22.9 g) and water (571 ml), and the mixture was stirred at about 50° C. for 5 hours stirred, then, the toluene layer was concentrated under reduced pressure. To the residue was added heptane (267 ml), methanol (534 ml) and water (267 ml), and the mixture was liquid-partitioned. The aqueous layer was liquid-partitioned by further adding heptane (267 ml), and the resulting aqueous layer was concentrated under reduced pressure to remove methanol. To the concentrated liquid was added sodium chloride (46 g), and the mixture was extracted twice with ethyl acetate (267 ml). The resultant ethyl acetate solution was concentrated under reduced pressure to obtain a title compound (277 g, yield 84%).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customInto a solution prepared
  3. additionwas dropped the above-described concentration residue at 55 to 75° C
  4. customthe mixture was reacted for 5 hours
  5. distillationwhile distilling components of lower boiling points off
  6. customAfter completion of the reaction, water (366 ml)
  7. additionwas added
  8. customthe liquid was partitioned
  9. additionTo the resultant toluene layer was added 98% sulfuric acid (22.9 g) and water (571 ml)
  10. stirringthe mixture was stirred at about 50° C. for 5 hours
  11. stirringstirred
  12. concentrationthe toluene layer was concentrated under reduced pressure
  13. additionTo the residue was added heptane (267 ml), methanol (534 ml) and water (267 ml)
  14. customthe mixture was liquid-partitioned
  15. customThe aqueous layer was liquid-partitioned
  16. additionby further adding heptane (267 ml)
  17. concentrationthe resulting aqueous layer was concentrated under reduced pressure
  18. customto remove methanol
  19. additionTo the concentrated liquid was added sodium chloride (46 g)
  20. extractionthe mixture was extracted twice with ethyl acetate (267 ml)
  21. concentrationThe resultant ethyl acetate solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-85b6c830c7ed496ebd13fa9b6b53dc08
Source dataset
uspto-grants-2011_05
Patent number
US07951977B2

Reaction notes

Loading…