Benzene → HCID 54075037, compound

HRID 1763862Notes

Reaction equation

HRID 1763862 reaction equation
[O:1]([C:8]1[CH:9]=[CH:10][C:11]2[CH2:12][C@H:13]3[N:24](C)[CH2:23][CH2:22][C@@:19]4([C:20]=2[CH:21]=1)[C@H:14]3[CH2:15][CH2:16][CH2:17][CH2:18]4)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:39]([O:41][CH2:42][C:43]([Cl:46])([Cl:45])[Cl:44])=[O:40]>CCOCC>[O:1]([C:8]1[CH:9]=[CH:10][C:11]2[CH2:12][C@H:13]3[N:24]([C:39]([O:41][CH2:42][C:43]([Cl:46])([Cl:45])[Cl:44])=[O:40])[CH2:23][CH2:22][C@@:19]4([C:20]=2[CH:21]=1)[C@H:14]3[CH2:15][CH2:16][CH2:17][CH2:18]4)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 11430Potassium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 15942836HCID 15942836, compound

Product 1

HCID 54075037HCID 54075037, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 2.3 g (0.007 mol) of (-)-3-phenoxy-N-methylmorphinan, 150 ml of benzene and 0.35 g of potassium carbonate was added dropwise, 3.3 g of 2,2,2-trichloroethyl chloroformate. The reaction mixture was stirred at reflux for 6 days. The mixture was diluted with ether and extracted with 4 N hydrochloric acid. The organic phase was washed with dilute ammonium hydroxide, water, and dried. Removal of solvent gave 3.4 g (99%) of the product (-)-3-phenoxy-N-trichlorocarbethoxymorphinan. For analysis, a sample of this compound was distilled, bp 230°-240°/0.05mmHg, [α]25D -119.65° (c 0.95, MeOH).

Workup

  1. additionwas added dropwise
  2. temperatureat reflux for 6 days
  3. extractionextracted with 4 N hydrochloric acid
  4. washThe organic phase was washed with dilute ammonium hydroxide, water
  5. customdried
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-bfdbf1eae6d442ef86689ea3236f5142
Source dataset
uspto-grants-1978_09
Patent number
US04113729

Reaction notes

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