2-Ethoxyphenol → HCID 13320282, compound

HRID 1262611Notes

Reaction equation

HRID 1262611 reaction equation
[CH2:1]([N:3]1[CH2:7][CH:6]2[O:8][CH:5]2[CH2:4]1)[CH3:2].[CH2:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[CH3:10]>Cl.C(Cl)Cl>[CH2:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][C@@H:6]1[CH2:7][N:3]([CH2:1][CH3:2])[CH2:4][C@H:5]1[OH:8])[CH3:10]

Participants

5

Reactant 2

HCID 667552-EthoxyphenolHCID 13320194N-ethyl-3,4-epoxypyrrolidine

Product 1

HCID 13320282HCID 13320282, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 17.0 g. (0.15 mole) of 1-ethyl-3,4-epoxypyrrolidine, 22.1 g. (0.16 mole) of o-ethoxyphenol and 3 drops of concentrated hydrochloric acid was heated on a steam bath overnight. The oil was dissolved in methylene chloride and washed with three 50-ml. portions of 5% sodium hydroxide and one 50-ml. portion of water. The methylene chloride solution was dried over anhydrous sodium sulfate, concentrated and chromatographed on silica gel to give 8.1 g. (21%) of an oil which crystallized on standing. The solid was recrystallized from cyclohexane to yield a tan solid, m.p. 73°-75° C.

Workup

  1. additionA mixture of 17.0 g
  2. washwashed with three 50-ml
  3. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customchromatographed on silica gel
  6. customto give 8.1 g
  7. custom(21%) of an oil which crystallized
  8. customThe solid was recrystallized from cyclohexane
  9. customto yield a tan solid, m.p. 73°-75° C.

Sources & evidence

ORD record
ord-df00938256eb466a96e82cfc0fba708d
Source dataset
uspto-grants-1984_06
Patent number
US04452809

Reaction notes

Loading…