Sodium Hydroxide → HCID 15295558, compound

HRID 1720136Notes

Reaction equation

HRID 1720136 reaction equation
[OH-].[Na+].[CH2:3]([C:10]1[CH:25]=[CH:24][C:13]([C:14]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]C)=[O:21])=[O:15])=[CH:12][CH:11]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]>C(O)C>[CH2:3]([C:10]1[CH:25]=[CH:24][C:13]([C:14]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[O:15])=[CH:12][CH:11]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22420395HCID 22420395, compound

Product 1

HCID 15295558HCID 15295558, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound is then prepared from the methyl ester as follows. 2N Sodium hydroxide (108 ml) is added to a solution of methyl 5-(4-n-heptylbenzoyl)pentanoate (22.8 g, 0.07 mole) in ethanol (216 ml) and the mixture heated under reflux for about 2 hours. The reaction mixture is cooled and extracted with ether (2×350 ml). The ether phase is discarded and the aqueous phase acidified (pH 2) with concentrated hydrochloric acid. The precipitate is collected by filtration, washed with water, and recrystallized from ethanol to give 5-(4-n-heptylbenzoyl) pentanoic acid (16.4 g) as colorless crystals, m.p. 80°-81° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for about 2 hours
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted with ether (2×350 ml)
  5. filtrationThe precipitate is collected by filtration
  6. washwashed with water
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-38cf630fbfca484eaa4073cb948c8dd0
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

Loading…