Sodium Hydroxide → 8-Acetyl-12-hydroxyheptadec-10-ynoic acid

HRID 839988Notes

Reaction equation

HRID 839988 reaction equation
[C:1]([C:4]([CH2:21][C:22]#[C:23][CH:24]([O:30]C(=O)C)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])C(OCC)=O)(=[O:3])[CH3:2].[OH-].[Na+]>O.CO>[C:1]([CH:4]([CH2:21][C:22]#[C:23][CH:24]([OH:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20322248Diethyl 2-acetyl-2-(4-acetoxy-2-nonyn-1-yl)azelate

Product 1

HCID 203222518-Acetyl-12-hydroxyheptadec-10-ynoic acidYield 36.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of diethyl 2-acetyl-2-(4-acetoxy-2-nonyn-1-yl)azelate (59.7 g., 0.128 mole) and sodium hydroxide (30 g., 0.75 mole) in water (200 ml.) and methanol (800 ml.) is heated at 60° for 16 hours. Most of the methanol is then distilled at reduced pressure and the residue is dissolved in water. The solution is acidified to Congo Red with hydrochloric acid and the oily product taken up in ether and dried over sodium sulfate. Evaporation of the ether leaves 41.1 g. of the crude product as a redish viscous oil. The product is purified by chromatography on 650 g. of silica gel with 2% methanol in chloroform as eluant. Fifteen grams of pure 8-acetyl-12-hydroxy-10-heptadecynoic acid is obtained as a yellow viscous oil; pmr (CDCl3) δ 0.90 (3H,t), 2.20 (3H,s CH3CO), 4.37 (1H,t HCO).

Workup

  1. distillationMost of the methanol is then distilled at reduced pressure
  2. dissolutionthe residue is dissolved in water
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of the ether
  5. customleaves 41.1 g
  6. customThe product is purified by chromatography on 650 g

Sources & evidence

ORD record
ord-65e90b70291d4bb6b9684775642b1437
Source dataset
uspto-grants-1978_06
Patent number
US04097504

Reaction notes

Loading…