Sulfuric Acid → HCID 15067586, compound

HRID 1614407Notes

Reaction equation

HRID 1614407 reaction equation
[OH-].[Na+].C([O:6][CH:7]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])/[CH:8]=[CH:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])(=O)C.S(=O)(=O)(O)O>CO>[OH:6][CH:7]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])/[CH:8]=[CH:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 15067584HCID 15067584, compound

Product 1

HCID 15067586HCID 15067586, compoundYield 35,239.898%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
24 °C

Procedure

0.3 ml of a 0.5 normal sodium hydroxide solution is added to a solution of 12 mg of 5-[2-[(1E,3E)-(5RS)-5-acetoxy-1,3-tridecadienyl]-phenyl]-pentanoic acid (produced in example 5) in 0.3 ml of methanol at 25° C. and stirred for 4 hours at 24° C. Then, it is cooled to 0° C. and acidified with a 0.5 normal sulfuric acid to pH=6. It is extracted four times with ethyl acetate, the organic phase is washed with water and dried on sodium sulfate. It is concentrated by evaporation in a vacuum, and the residue is chromatographed on silica gel. With ether/hexane (7+3) as a mobile solvent, 3.8 g of the title compound is obtained as a colorless oil.

Workup

  1. temperatureThen, it is cooled to 0° C.
  2. extractionIt is extracted four times with ethyl acetate
  3. washthe organic phase is washed with water
  4. customdried on sodium sulfate
  5. concentrationIt is concentrated by evaporation in a vacuum
  6. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-6faaf8a294fb43428958531c9e8fccab
Source dataset
uspto-grants-1993_03
Patent number
US05196570

Reaction notes

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