Potassium Hydroxide → HCID 14501714, compound

HRID 1904678Notes

Reaction equation

HRID 1904678 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[OH:9])[CH:5]=[CH:6][CH:7]=1.Cl.Cl[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.[OH-].[K+]>O.C(O)C>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH:3]=2)[OH:9])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 14501713HCID 14501713, compound

Product 1

HCID 14501714HCID 14501714, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3.7 g (0.016 mol) 1-(3-hydroxyphenyl)-1-(4-methoxyphenyl)methanol, 3.4 g (0.016 mol) 2-chloromethylquinoline hydrochloride and 2 g (0.036 mol) KOH in 5 ml water and 50 ml ethanol was heated over steam bath for a period of 4 hours. Reaction mixture was concentrated to dryness and slurried into water and extracted with methylene chloride. The methylene chloride extract was washed with water, dried over MgSO4 and concentrated to dryness under reduced pressure to obtain oily material. Repeated recrystallization from ethyl acetate, acetonitrite and isopropanol gave desired produce 1.1 g. m.p. 70°-80° C.

Workup

  1. temperaturewas heated over steam bath for a period of 4 hours
  2. customReaction mixture
  3. concentrationwas concentrated to dryness
  4. extractionextracted with methylene chloride
  5. extractionThe methylene chloride extract
  6. washwas washed with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated to dryness under reduced pressure
  9. customto obtain oily material
  10. customrecrystallization from ethyl acetate
  11. customacetonitrite and isopropanol gave
  12. customdesired produce 1.1 g

Sources & evidence

ORD record
ord-47cd1dbc7e4547b4bbb133a574d17a51
Source dataset
uspto-grants-1989_06
Patent number
US04839369

Reaction notes

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