1-Bromopropane → HCID 20352632, compound

HRID 372006Notes

Reaction equation

HRID 372006 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5].[OH-].[K+].Br[CH2:18][CH2:19][CH3:20]>C(O)CCC>[CH2:18]([O:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5])[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 14797Potassium HydroxideHCID 30160863-(2-Hydroxybenzoyl)propionic acid

Product 1

HCID 20352632HCID 20352632, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

3-(o-Hydroxybenzoyl)propionic acid (14.6 g.) was dissolved in n-butanol (300 ml.) containing 85% potassium hydroxide (10 g.) and the resultant solution was treated with 1-bromopropane (24.6 g.) and the mixture heated at reflux temperature for 4 hours. It was then cooled, filtered to remove potassium bromide and the filtrate washed with cold water. The butanol was evaporated at reduced pressure and the residual oil distilled at 0.3 mm when the fraction b.p. 160°-180° C was collected (16.4 g.). This was dissolved in methanol (50 ml.), treated with 20% sodium hydroxide solution (20 ml.) and heated on the steambath for 30 minutes. The methanol was boiled off and the residue diluted with water (250 ml.) and acidified with hydrochloric acid. The precipitated acid was collected and crystallised from 50% methanol. It had m.p. 77°-79° C (Yield 13.3 g.).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux temperature for 4 hours
  3. temperatureIt was then cooled
  4. filtrationfiltered
  5. customto remove potassium bromide
  6. washthe filtrate washed with cold water
  7. customThe butanol was evaporated at reduced pressure
  8. distillationthe residual oil distilled at 0.3 mm when the fraction b.p. 160°-180° C
  9. customwas collected (16.4 g.)
  10. dissolutionThis was dissolved in methanol (50 ml.)
  11. additiontreated with 20% sodium hydroxide solution (20 ml.)
  12. temperatureheated on the steambath for 30 minutes
  13. additionthe residue diluted with water (250 ml.)
  14. customThe precipitated acid was collected
  15. customcrystallised from 50% methanol

Sources & evidence

ORD record
ord-aa9638a7b6f74518b60d146a855110bb
Source dataset
uspto-grants-1978_05
Patent number
US04088762

Reaction notes

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