2,6-Dichlorophenol → HCID 13320220, compound

HRID 1381223Notes

Reaction equation

HRID 1381223 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.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=1[OH:22]>C(Cl)Cl>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[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

4

Reactant 2

HCID 68992,6-DichlorophenolHCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexane

Product 1

HCID 13320220HCID 13320220, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 35.0 g. of 1-benzyl-3,4-epoxypyrrolidine and 32.6 g. of 2,6-dichlorophenol was heated at 125° C. for 3 hr. The mixture was cooled, dissolved in methylene chloride and extracted with dilute sodium hydroxide. The residue after the solvent was evaporated was purified by column chromatography. The product was eluted with 30% ethyl acetate in benzene and crystallized from cyclohexane. Yield was 43 g (64%), m.p. 78°-80° C.

Workup

  1. additionA mixture of 35.0 g
  2. temperatureThe mixture was cooled
  3. extractionextracted with dilute sodium hydroxide
  4. customThe residue after the solvent was evaporated
  5. customwas purified by column chromatography
  6. washThe product was eluted with 30% ethyl acetate in benzene
  7. customcrystallized from cyclohexane

Sources & evidence

ORD record
ord-a42c59e244a0486f84ed1219088fae32
Source dataset
uspto-grants-1986_04
Patent number
US04585785

Reaction notes

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