4-Chlorophenol → HCID 13320208, compound

HRID 1381219Notes

Reaction equation

HRID 1381219 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

Sources & evidence

ORD record
ord-2d1577bcce8144c1ad775127ffb44947
Source dataset
uspto-grants-1986_04
Patent number
US04585785

Reaction notes

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