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

HRID 1857053Notes

Reaction equation

HRID 1857053 reaction equation
Cl[CH2:2][CH:3]1[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[O:4]1.[Br-].[Na+].[C:12]([O-:15])(=[O:14])[CH3:13].[Na+]>CN(C)C=O>[C:12]([O:15][CH2:2][CH:3]1[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[O:4]1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 203744-(Chloromethyl)-2,2-dimethyl-1,3-dioxolaneHCID 253881Sodium BromideHCID 517045Sodium Acetate

Product 1

HCID 252333(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl acetateYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 4-chloromethyl-2,2-dimethyl-1,3-dioxolane (51.60 g, 0.343 mol) prepared by Example 1 and N,N-dimethylformamide (400 ml), sodium bromide (37.04 g, 0.36 mol) and sodium acetate (29.53 g, 0.36 mol) were added 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. Water was added to the residue and it was extracted with toluene and the extract was washed with saturated brine, dried over anhydrous sodium sulfate and condensed in vacuo. The crude product was distilled to give 38.24 g of 4-acetoxymethyl-2,2-dimethyl-1,3-dioxolane (yield 64%, b.p. 81° C. at 12 mmHg).

Workup

  1. additionwere added
  2. temperatureAfter cooling
  3. filtrationthe salt was filtered off
  4. customN,N-dimethylformamide was removed in vacuo
  5. additionWater was added to the residue and it
  6. extractionwas extracted with toluene
  7. washthe extract was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate and condensed in vacuo
  9. distillationThe crude product was distilled

Sources & evidence

ORD record
ord-28926dcc5a014840b69822363bfc7480
Source dataset
uspto-grants-2000_11
Patent number
US06143908

Reaction notes

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