2-Ethoxyphenol → HCID 13320246, compound

HRID 1381229Notes

Reaction equation

HRID 1381229 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.[CH2:14]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])[CH3:15]>Cl.C(Cl)Cl>[CH2:14]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][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])[CH3:15]

Participants

5

Reactant 2

HCID 667552-EthoxyphenolHCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexane

Product 1

HCID 13320246HCID 13320246, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 45.5 g. (0.26 mole) of 1-benzyl-3,4- epoxypyrrolidine (60 g. of 76% epoxide), 48 g. (0.35 mole) of o-ethoxyphenol and 8 drops of concentrated hydrochloric acid was heated at 145° C. for 16 hr. The mixture was cooled, dissolved in methylene chloride and washed with dilute sodium hydroxide solution. The methylene chloride layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was chromatographed on 1 kg. of silica gel using 20% acetone in benzene as the eluent. Two recrystallizations from cyclohexane gave 8.0 g. (10%) of tan needles, m.p. 88.5°-90.0° C.

Workup

  1. additionA mixture of 45.5 g
  2. temperatureThe mixture was cooled
  3. washwashed with dilute sodium hydroxide solution
  4. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was chromatographed on 1 kg
  7. customTwo recrystallizations from cyclohexane
  8. customgave 8.0 g

Sources & evidence

ORD record
ord-b9ec5486b60a4fdf9a348ef4b3919537
Source dataset
uspto-grants-1986_04
Patent number
US04585785

Reaction notes

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