Chloroform → HCID 18927887, compound

HRID 274170Notes

Reaction equation

HRID 274170 reaction equation
C([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=O)C.C(Cl)(Cl)Cl.ClC1C=CC=[C:30]([C:34]([O:36]O)=[O:35])C=1.S([O-])(O)=O.[Na+]>ClCCl>[C:34]([O:36][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)(=[O:35])[CH3:30]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 70297m-Chloroperbenzoic acid2×HCID 15027156HCID 15027156, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 18927887HCID 18927887, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

29.6 g (0.1 mol) of (-)-4-acetyl-4'-(2-acetoxypropyl)biphenyl (XIX-13) {[α]D20 -9.9° (C=1, CHCl3)} was charged into a four necked-flask provided with a thermometer and an agitator, and dissolved by adding 200 ml of dichloromethane. 20.7 g (0.12 mol) of m-chloroperbenzoic acid was added in this solution and agitated at reflux for 8 hours. After excess of m-chloroperbenzoic acid was decomposed by adding 10% aqueous solution of sodium hydrogen sulfite to the reaction mixture, the organic layer was washed with 10% aqueous solution of sodium bicarbonate and then with water, and dried an anhydrous magnesium sulfate. The resulting dichloromethane solution was concentrated under the reduced pressure to provide 30.2 g (yield: 97%) of (-)-4-acetoxy-4'-(2-acetoxypropyl)biphenyl (XVIII-13).

Workup

  1. customprovided with a thermometer
  2. dissolutionan agitator, and dissolved
  3. temperatureat reflux for 8 hours
  4. washthe organic layer was washed with 10% aqueous solution of sodium bicarbonate
  5. dry with materialwith water, and dried an anhydrous magnesium sulfate
  6. concentrationThe resulting dichloromethane solution was concentrated under the reduced pressure

Sources & evidence

ORD record
ord-e3860ca5db424aec8de87b77789967cd
Source dataset
uspto-grants-1995_02
Patent number
US05389293

Reaction notes

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