Acetone → 2,2-Dimethyl-4-((phenylmethoxy)methyl)-1,3-dioxolane

HRID 1955348Notes

Reaction equation

HRID 1955348 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Cl[CH2:14][CH:15]([OH:18])[CH2:16][OH:17].Cl.[CH3:20][C:21]([CH3:23])=O>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C.CN(C=O)C>[CH2:1]([O:8][CH2:14][CH:15]1[CH2:16][O:17][C:21]([CH3:23])([CH3:20])[O:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

10

Reactant 6

HCID 180AcetoneHCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 72903-Chloro-1,2-propanediolHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 857952,2-Dimethyl-4-((phenylmethoxy)methyl)-1,3-dioxolaneYield 52%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

Benzyl alcohol (21.93 g, 0.203 mol) was dropped under ice cooling in a suspension of 60% sodium hydride (3.92 g, 0.103 mol) and DMF (100 ml). After emission of hydrogen gas, therein a DMF solution (10 ml) of 3-chloro-1,2-propanediol (5.692 g, 0.052 mol) was dropped. The reaction temperature was raised to 60° C. and the mixture was stirred under heating for 2 hours. After completion of the reaction the reaction mixture was cooled on ice bath and neutralized with 6% hydrochloric acid. After removal of water and DMF in vacuo, ethyl acetate was added to the residue, the insoluble materials were filtered off and the filtrate was condensed in vacuo. Thereto acetone (500 ml) and p-toluenesulfonic acid (0.386 g) were added and the solution was stirred for 3 hours at 25° C. After the reaction was over, the mixture was neutralized with triethylamine. After stirring for 5 minutes, acetone was removed by distillation. The crude product was distilled to give 5.949 g of 4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane (yield 52%, b.p. 110° C. at 0.3 mmHg).

Workup

  1. temperatureunder heating for 2 hours
  2. customAfter completion of the reaction the reaction mixture
  3. temperaturewas cooled on ice bath
  4. customAfter removal of water and DMF in vacuo, ethyl acetate
  5. additionwas added to the residue
  6. filtrationthe insoluble materials were filtered off
  7. customcondensed in vacuo
  8. stirringthe solution was stirred for 3 hours at 25° C
  9. stirringAfter stirring for 5 minutes
  10. customacetone was removed by distillation
  11. distillationThe crude product was distilled

Sources & evidence

ORD record
ord-eb2c1dfc16cc48bb8be3a17cc5e774a0
Source dataset
uspto-grants-2000_09
Patent number
US06124479

Reaction notes

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