Carbon Dioxide → HCID 20280999, compound

HRID 905303Notes

Reaction equation

HRID 905303 reaction equation
[Br:1]Br.[C:3]([O:9][CH2:10][C:11]1[CH:12]=[C:13]([C:24](=[O:26])[CH3:25])[CH:14]=[CH:15][C:16]=1[O:17][C:18](=[O:23])[CH2:19][CH2:20][CH2:21][CH3:22])(=[O:8])[CH2:4][CH2:5][CH2:6][CH3:7].C(=O)=O>C(Cl)(Cl)Cl>[C:3]([O:9][CH2:10][C:11]1[CH:12]=[C:13]([C:24](=[O:26])[CH2:25][Br:1])[CH:14]=[CH:15][C:16]=1[O:17][C:18](=[O:23])[CH2:19][CH2:20][CH2:21][CH3:22])(=[O:8])[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 24408BromineHCID 20248379HCID 20248379, compound

Product 1

HCID 20280999HCID 20280999, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of bromine (4.2 g.) in chloroform (20 ml.) was added dropwise to a cooled stirred solution of 3'-valeryloxymethyl-4'-valeryloxyacetophenone (8.5 g.) in chloroform (100 ml.). During the addition, the temperature was maintained at 0°-5° C. by the addition of small pieces of solid carbon dioxide. The solution was then washed with 10% w/v sodium carbonate solution (3×100 ml.) water (2×100 ml.) and saturated brine (100 ml.). The organic phase was dried (MgSO4), filtered, and evaporated yielding 3'-valeryloxymethyl-4'-valeryloxy-2-bromoacetophenone (6 g., 57%), which was judged to be sufficiently pure by IR and TLC [SiO2 : 50 v/v EtOAc/petrol (60°-80°)] for use without further purification or characterisation.

Workup

  1. additionDuring the addition
  2. washThe solution was then washed with 10% w/v sodium carbonate solution (3×100 ml.) water (2×100 ml.) and saturated brine (100 ml.)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-4c0a80faa1554b9193af183e05ae089e
Source dataset
uspto-grants-1983_12
Patent number
US04423070

Reaction notes

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