Phenol → HCID 13320198, compound

HRID 1262591Notes

Reaction equation

HRID 1262591 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.[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O.C(OCC)C>[O:20]([C@@H:11]1[CH2:12][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][C@H:10]1[OH:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 996PhenolHCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexane

Product 1

HCID 13320198HCID 13320198, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 12.3 g. of 1-benzyl-3,4-epoxypyrrolidine, 13.2 g. of phenol 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. ethyl ether. The ethereal solution was extracted with 2×50 ml. of 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 analytically pure product melting at 101°-104° C. The yield was 24% of theory.

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. washof 5% 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

Sources & evidence

ORD record
ord-b082c1e0640141eb8678052ec9c0ee59
Source dataset
uspto-grants-1984_06
Patent number
US04452809

Reaction notes

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