1-(2-Hydroxy-5-methoxyphenyl)ethan-1-one → HCID 19736723, compound

HRID 326295Notes

Reaction equation

HRID 326295 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11]>C(O)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]2[O:1][C:2]3([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]3)[CH2:11][C:10](=[O:12])[C:3]=2[CH:4]=1

Participants

3

Reactant 1

HCID 697141-(2-Hydroxy-5-methoxyphenyl)ethan-1-one

Product 1

HCID 19736723HCID 19736723, compoundYield 182.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (2'-hydroxy-5'methoxyphenyl)ethanone (3.32 g, 20 mmol) and cyclohexanonepyrrolidine (enamine form) (3.18 g, 21 mmol) in dry ethanol (40 ml) is heated to reflux for 1.5 hours under nitrogen gas. The solvent is removed by distillation, and the residue is dissolved in diethyl ether, washed with dilute HCl and then water, dried, and concentrated. The residue is placed on a silica gel column and eluted with a mixture of ethyl acetate and hexane (1:2) to obtain the title compound as thick syrup (4.5 g, yield 91.3%). ##STR8##

Workup

  1. temperatureto reflux for 1.5 hours under nitrogen gas
  2. customThe solvent is removed by distillation
  3. dissolutionthe residue is dissolved in diethyl ether
  4. washwashed with dilute HCl
  5. dry with materialwater, dried
  6. concentrationconcentrated
  7. washeluted with a mixture of ethyl acetate and hexane (1:2)

Sources & evidence

ORD record
ord-67d662d6a25843d48f08f48c00549da6
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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