4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane → (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl benzoate

HRID 1857051Notes

Reaction equation

HRID 1857051 reaction equation
[Br-].[Na+].[C:3]([O-:11])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Na+].Cl[CH2:14][CH:15]1[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]1>CN(C)C=O>[C:3]([O:11][CH2:14][CH:15]1[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 203744-(Chloromethyl)-2,2-dimethyl-1,3-dioxolaneHCID 253881Sodium BromideHCID 517055Sodium Benzoate

Product 1

HCID 571151(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl benzoateYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Then, sodium bromide (43.01 g, 0.42 mol) and sodium benzoate (60.24 g, 0.42 mol) were added to a mixture of the above 4-chloromethyl-2,2-dimethyl-1,3-dioxolane (60.02 g, 0.39 mol) and N,N-dimethylformamide (600 ml) and the resulting mixture was stirred for 15 hours 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 crude 4-benzoyloxymethyl-2,2-dimethyl-1,3-dioxolane (yield 90%).

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-461c76891129427badf074aa61f0f69f
Source dataset
uspto-grants-2000_11
Patent number
US06143908

Reaction notes

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