Sodium Hydroxide → HCID 54399557, compound

HRID 1391159Notes

Reaction equation

HRID 1391159 reaction equation
[C:1]([C:4](C(OCC)=O)([CH2:19][CH:20]=[CH:21][CH:22]([O:28]C(=O)C)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:5][CH2:6][CH2:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=1)(=[O:3])[CH3:2].[OH-].[Na+]>O.C(O)C>[C:1]([CH:4]([CH2:19][CH:20]=[CH:21][CH:22]([OH:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:17][CH:18]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53719411HCID 53719411, compound

Product 1

HCID 54399557HCID 54399557, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 4-(4-acetyl-4-ethoxycarbonyl-8-acetoxytridec-6-en-1-yl)benzoate (50.2 g., 0.1 mole) and sodium hydroxide (28.0 g., 0.7 mole) in water (300 ml.) and ethanol (350 ml.) is boiled under reflux for 3 hours. Solvents are removed under reduced pressure, the residue is dissolved in water, and the solution extracted with ether. The aqueous layer is acidified with concentrated hydrochloric acid to the Congo Red endpoint. The crude product separates as an oil. It is isolated in pure condition by column chromatography on silica gel with 4% methanol in chloroform as the eluant. 4-(4-Acetyl-8-hydroxytridec-6-en-1-yl)benzoic acid is obtained as a yellow, very viscous oil.

Workup

  1. temperatureunder reflux for 3 hours
  2. customSolvents are removed under reduced pressure
  3. dissolutionthe residue is dissolved in water
  4. extractionthe solution extracted with ether
  5. customIt is isolated in pure condition by column chromatography on silica gel with 4% methanol in chloroform as the eluant

Sources & evidence

ORD record
ord-e150445a1efc4d999c84b1a2eeba721a
Source dataset
uspto-grants-1979_02
Patent number
US04140861

Reaction notes

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