4-Methoxyphenol → HCID 13320244, compound

HRID 1262604Notes

Reaction equation

HRID 1262604 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.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1>O.C(Cl)Cl>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][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:18][CH:17]=1

Participants

5

Reactant 2

HCID 90154-MethoxyphenolHCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexane

Product 1

HCID 13320244HCID 13320244, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 17.5 g. (0.10 mole) of 1-benzyl-3,4-epoxypyrrolidine, 13.4 g. (0.11 mole) of p-methoxyphenol, and 3 drops of water was heated on a steam bath overnight. The dark residue was dissolved in methylene chloride and the solution was washed with two 50-ml. portions of 5% sodium hydroxide. The methylene chloride layer was dried over anhydrous sodium sulfate and concentrated to give 23.7 g. of viscous dark oil. This oil was chromatographed on 480 g. of silica gel 60 and the product was eluted with a 1:1 benzene:ether solution. The appropriate fractions were concentrated to give 10.0 g. of a yellow oil which crystallized upon scratching. The solid was recrystallized from cyclohexane to yield 7.2 g. (24%) tan solid, m.p. 84°-5° C.

Workup

  1. additionA mixture of 17.5 g
  2. washthe solution was washed with two 50-ml
  3. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto give 23.7 g
  6. customThis oil was chromatographed on 480 g
  7. washof silica gel 60 and the product was eluted with a 1:1 benzene
  8. concentrationThe appropriate fractions were concentrated
  9. customto give 10.0 g
  10. customof a yellow oil which crystallized
  11. customThe solid was recrystallized from cyclohexane
  12. customto yield 7.2 g

Sources & evidence

ORD record
ord-272d87270ec54ba5bc1b8cdfa9ff9101
Source dataset
uspto-grants-1984_06
Patent number
US04452809

Reaction notes

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