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

HRID 1857061Notes

Reaction equation

HRID 1857061 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].Br[CH2:12][CH: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][CH: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 1697594-(Bromomethyl)-2,2-dimethyl-1,3-dioxolaneHCID 517055Sodium Benzoate

Product 1

HCID 571151(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl benzoateYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Then, sodium benzoate (50.44 g, 0.35 mol) were added to a mixture of 4-bromomethyl-2,2-dimethyl-1,3-dioxolane (58.52 g, 0.3 mol) and N,N-dimethylformamide (500 ml) and the resulting mixture was stirred for 15 hours at 150° C. After cooling the salt was filtered 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 64.5 g of crude 4-benzoyloxymethyl-2,2-dimethyl-1,3-dioxolane (yield 91%).

Workup

  1. temperatureAfter cooling the salt
  2. filtrationwas filtered
  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-b283fed5cf0f464faa6011368a0141de
Source dataset
uspto-grants-2000_11
Patent number
US06143908

Reaction notes

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