Guaiacol → HCID 13320242, compound

HRID 1262603Notes

Reaction equation

HRID 1262603 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([O:21][CH3:22])[C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)[OH:16]>>[CH3:22][O:21][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[O:16][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

3

Reactant 2

HCID 460GuaiacolHCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexane

Product 1

HCID 13320242HCID 13320242, compoundYield 27%

Procedure

A mixture of 40 g. of crude 1-benzyl-3,4-epoxypyrrolidine and 70 g. of guaiacol was heated at 120° C. for 20 hr. Aspirator vacuum was then used to distill off the excess guaiacol. The residue was dissolved in methylene chloride and extracted with dilute sodium hydroxide. The methylene chloride solution was dried over anhydrous sodium sulfate and the solvent was evaporated. The residue weighed 54 g., was chromatographed on 1 kg. of silica gel. The product was eluted with 50% ethyl acetate in benzene and crystallized from cyclohexane. The m.p. was 115°-117° C. and the yield was 27%.

Workup

  1. additionA mixture of 40 g
  2. distillationto distill off the excess guaiacol
  3. dissolutionThe residue was dissolved in methylene chloride
  4. extractionextracted with dilute sodium hydroxide
  5. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. custom, was chromatographed on 1 kg
  8. washThe product was eluted with 50% ethyl acetate in benzene
  9. customcrystallized from cyclohexane

Sources & evidence

ORD record
ord-a2b1e888f07041d19b1150e86384d778
Source dataset
uspto-grants-1984_06
Patent number
US04452809

Reaction notes

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