4-Chlorophenol → HCID 13320208, compound

HRID 1262595Notes

Reaction equation

HRID 1262595 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]2[O:13][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1>O.C(OCC)C>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C@@H:11]2[CH2:12][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][C@H:10]2[OH:13])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 46844-ChlorophenolHCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexane

Product 1

HCID 13320208HCID 13320208, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 12.3 g. of 1-benzyl-3,4-epoxypyrrolidine, 18.0 g. of p-chlorophenol and 3 drops of water was heated at 120° C. under nitrogen gas for 20 hr. The mixture was cooled and dissolved in 100 ml. diethyl ether. The ethereal solution was extracted with 2×50 ml. 5% sodium hydroxide and then washed with water. After being dried with anhydrous sodium sulfate, the solvent was evaporated and the residue weighed 14.3 g. Two crystallizations from cyclohexane gave 4.7 g (29%) of analytically pure product which melted at 101°-104° C.

Workup

  1. additionA mixture of 12.3 g
  2. temperatureThe mixture was cooled
  3. dissolutiondissolved in 100 ml
  4. extractionThe ethereal solution was extracted with 2×50 ml
  5. wash5% sodium hydroxide and then washed with water
  6. dry with materialAfter being dried with anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customTwo crystallizations from cyclohexane
  9. customgave 4.7 g (29%) of analytically pure product which melted at 101°-104° C.

Sources & evidence

ORD record
ord-095a7b0438694b1c9218e2b9ebe0dad6
Source dataset
uspto-grants-1984_06
Patent number
US04452809

Reaction notes

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