Ethyl Acetate → HCID 54121018, compound

HRID 2254319Notes

Reaction equation

HRID 2254319 reaction equation
[C:1]1([CH:7]2[O:11][CH:10]([CH2:12][O:13][CH3:14])[CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:15]N1C(=O)CCC1=O.CCCCCCC.C(OCC)(=O)C>ClC(Cl)C>[C:7]([O:11][CH:10]([CH2:12][O:13][CH3:14])[CH2:9][Br:15])(=[O:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 67184N-bromobutanimideHCID 14708829HCID 14708829, compound

Product 1

HCID 54121018HCID 54121018, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 13.6 g (0.07 mol) of 2-phenyl 4-methoxymethyl 1,3-dioxolane (S) (Austr. J. Chem. 761, 29, 1976) in 40 ml of dichloroethane, are gradually added 12.5 g (0.07 mol) of N-bromosuccinimide while keeping temperature at 25° C. After 1 h of stirring, the reaction medium is poured on water. The organic phase is washed with a solution of sodium thiosulphate, and then with water, dried over magnesium sulphate and concentrated. The product is obtained with a 93% yield, after chromatography (Silica, Heptane:60. Ethyl acetate:40).

Workup

  1. customat 25° C
  2. additionthe reaction medium is poured on water
  3. washThe organic phase is washed with a solution of sodium thiosulphate
  4. dry with materialwith water, dried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe product is obtained with a 93% yield

Sources & evidence

ORD record
ord-4d3e7080da0d43849075a7612bfcbf77
Source dataset
uspto-grants-1993_08
Patent number
US05235063

Reaction notes

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