3-Chloro-1,2-propanediol → 3-[p-(2,3-Dihydroxypropoxy)benzoyl]indole

HRID 247557Notes

Reaction equation

HRID 247557 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[CH2:22][CH:23]([OH:26])[CH2:24][OH:25]>O>[OH:26][CH:23]([CH2:24][OH:25])[CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)=[O:7])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 72903-Chloro-1,2-propanediolHCID 14798Sodium HydroxideHCID 30626713-(p-Hydroxy)benzoyl indole

Product 1

HCID 136694903-[p-(2,3-Dihydroxypropoxy)benzoyl]indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

11 g of 3-(p-hydroxybenzoyl)indole and 7.43 g of sodium hydroxide were dissolved in 10 ml of water. 20.51 g of 3-chloro-1,2-propandiol was added to the solution followed by reflux with stirring for 3 hours in oil bath. After cooling, the solution was evaporated to dryness. The residue was purified by column chromatography on silica gel. After recrystallization from ethyl acetate, 3-[p-(2,3-dihydroxypropoxy)benzoyl]indole (compound 16) was obtained in the form of white crystals. (Yield: 13.8%).

Workup

  1. temperatureby reflux
  2. temperatureAfter cooling
  3. customthe solution was evaporated to dryness
  4. customThe residue was purified by column chromatography on silica gel
  5. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-0832719b940f4026b165b37c2b01e781
Source dataset
uspto-grants-1987_11
Patent number
US04708961

Reaction notes

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