Sodium Hydroxide → HCID 22759245, compound

HRID 329294Notes

Reaction equation

HRID 329294 reaction equation
[C:1]([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([OH:32])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]CC)=[O:12])(=[O:3])[CH3:2].[OH-].[Na+]>O.CO>[C:1]([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([OH:32])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:31])[F:29])[CH:23]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22759220HCID 22759220, compound

Product 1

HCID 22759245HCID 22759245, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 8-acetyl-12-hydroxy-13-(3-trifluoromethylphenoxy)tridecanoate (17.4 g., 0.038 mole) and sodium hydroxide (4 g., 0.1 mole) in water (30 ml.) and methanol (120 ml.) is heated at 60° for 16 hours. Most of the methanol is then removed by distillation in vacuo. The residue is dissolved in 150 ml. of water and extracted with ether. The aqueous solution is acidified with concentrated hydrochloric acid. The oily product is taken up in ether and dried over sodium sulfate. Ether is evaporated in vacuo to leave the title compound as a viscous oil weighing 12.9 g. The product is purified by column chromatography on 200 g. of silica gel with 2% methanol in chloroform as eluant; pmr (CDCl3) δ 2.10 (3H, s CH3CO); 3.95 (3H, broad s CHO and CH2O); 6.75 (2H, s OH and CO2H).

Workup

  1. customMost of the methanol is then removed by distillation in vacuo
  2. dissolutionThe residue is dissolved in 150 ml
  3. extractionof water and extracted with ether
  4. dry with materialdried over sodium sulfate
  5. customEther is evaporated in vacuo

Sources & evidence

ORD record
ord-99442427c93a4644ad3af600ab89f1c5
Source dataset
uspto-grants-1977_04
Patent number
US04020177

Reaction notes

Loading…