Water → HCID 70239352, compound

HRID 1596610Notes

Reaction equation

HRID 1596610 reaction equation
[Cl:1][C:2](Cl)([Cl:6])C([O-])=O.[Na+].[C:9]([O:12][CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:11])[CH3:10].O>COCCOCCOC>[C:9]([O:12][CH2:13][C@H:14]1[C@H:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:2]1([Cl:6])[Cl:1])(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 5282110(E)-3-Phenylallyl acetateHCID 23681045Sodium Trichloroacetate

Product 1

HCID 70239352HCID 70239352, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

A solution of sodium trichloroacetate (27.8 g, 150 mmol) in diglyme (20 ml) was added dropwise over 1 hour to a solution of trans-cinnamyl acetate (8.81 g, 50 mmol) in diglyme (80 ml) at 120° C. to 135° C. and the reaction mixture was heated at 120° C. to 125° C. for 1 hour. The reaction mixture was cooled to room temperature, poured into water (300 ml), extracted with n-hexane (300 ml+3×50 ml) and dried over MgSO4. The solvent was removed and the residue was distilled under vacuum affording the title compound (11.0 g, 76% yield, b.p. 104-105° C. (0.15 mmHg)).

Workup

  1. temperaturethe reaction mixture was heated at 120° C. to 125° C. for 1 hour
  2. extractionextracted with n-hexane (300 ml+3×50 ml)
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed
  5. distillationthe residue was distilled under vacuum

Sources & evidence

ORD record
ord-1216ad637b6f48b7b7d6ca0ef7b1df42
Source dataset
uspto-grants-2001_09
Patent number
US06291520B1

Reaction notes

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