2,3-Dimethylphenol → HCID 13320238, compound

HRID 1262601Notes

Reaction equation

HRID 1262601 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][C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=1[OH:22]>Cl.C(Cl)Cl>[CH3:14][C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=1[O:22][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]

Participants

5

Reactant 2

HCID 106872,3-DimethylphenolHCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexane

Product 1

HCID 13320238HCID 13320238, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 17.5 g. (0.10 mole) of 1-benzyl-3,4-epoxypyrrolidine, 18.3 g. (0.15 mole) of 2,3-dimethylphenol and 2 drops of concentrated hydrochloric acid was heated at 120° C. under a nitrogen atmosphere overnight. The reaction mixture was dissolved in methylene chloride and washed with four 100-ml portions of 5% sodium hydroxide and once with water. The methylene chloride layer was dried over anhydrous sodium sulfate-potassium hydroxide and concentrated to give 28.6 g. of dark oil as residue. This oil was chromatographed on 600 g. of silica gel and the product was eluted with an acetone-benzene solution. The appropriate fractions were concentrated to give an oil which crystallized upon standing. This solid was recrystallized from ligroin to give 9.1 g. (31%) of white solid, m.p. 100°-4° C.

Workup

  1. additionA mixture of 17.5 g
  2. washwashed with four 100-ml portions of 5% sodium hydroxide and once with water
  3. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate-potassium hydroxide
  4. concentrationconcentrated
  5. customto give 28.6 g
  6. customThis oil was chromatographed on 600 g
  7. washof silica gel and the product was eluted with an acetone-benzene solution
  8. concentrationThe appropriate fractions were concentrated
  9. customto give an oil which
  10. customcrystallized
  11. customThis solid was recrystallized from ligroin
  12. customto give 9.1 g

Sources & evidence

ORD record
ord-9d7371c83ef44abbb9d99c9fb07a37c5
Source dataset
uspto-grants-1984_06
Patent number
US04452809

Reaction notes

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