Methanol → 8-Oxo-5-eicosynoic Acid

HRID 1165248Notes

Reaction equation

HRID 1165248 reaction equation
[OH:1][CH:2]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:3][C:4]#[C:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].CCOCC.CO>CC(C)=O>[O:1]=[C:2]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:3][C:4]#[C:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 3283Diethyl EtherHCID 147482558-Hydroxy-5-eicosynoic acid

Product 1

HCID 147482608-Oxo-5-eicosynoic Acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4.22 g of 8-hydroxy-5-eicosynoic acid, the product of Example 1d, in 200 ml of acetone with vigorous stirring at 5° was added 5.5 ml of Jone's reagent (2.67M). The reaction mixture was stirred for 30 min and then 700 ml of Et2O and 2 ml of MeOH was added and stirred for additional 3 min. The resulting reaction mixture was washed with H2O, saturated NaCl solution and dried over MgSO4. The crude product after removal of solvent was recrystallized in cyclohexane to yield the title compound, mp 79°-80.5°.

Workup

  1. stirringstirred for additional 3 min
  2. customThe resulting reaction mixture
  3. washwas washed with H2O, saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. customThe crude product after removal of solvent
  6. customwas recrystallized in cyclohexane

Sources & evidence

ORD record
ord-e492df31e6cc4ebea73dde5da3ff4333
Source dataset
uspto-grants-1990_03
Patent number
US04908384

Reaction notes

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