Sulfuric Acid → HCID 15067633, compound

HRID 1614408Notes

Reaction equation

HRID 1614408 reaction equation
[OH-].[Na+].C([O:6][CH:7]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])/[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][CH2:22][OH:23])(=O)C.S(=O)(=O)(O)O>CO>[OH:6][CH:7]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])/[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][CH2:22][OH:23]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 15067580HCID 15067580, compound

Product 1

HCID 15067633HCID 15067633, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

6.7 ml of a 0.5 normal sodium hydroxide solution is added to a solution of 270 mg of 5-[2-[(1E,3E)-(5RS)-5-acetoxy-1,3-tridecadienyl]-phenyl]-pentan-1-ol (produced in example 1) in 11.7 ml of methanol and the reaction mixture is stirred for 16 hours at 25° C. Then, it is cooled to 0° C. and acidified with a 0.5 normal sulfuric acid to pH=6. It is extracted three times with methylene chloride and the organic phase is dried on sodium sulfate. It is concentrated by evaporation in a vacuum, and the residue is chromatographed on silica gel. With hexane/50-80% of ethyl acetate as a mobile solvent, 184 mg of the title compound is obtained as a colorless oil.

Workup

  1. temperatureThen, it is cooled to 0° C.
  2. extractionIt is extracted three times with methylene chloride
  3. customthe organic phase is dried on sodium sulfate
  4. concentrationIt is concentrated by evaporation in a vacuum
  5. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-418e4465b87e4e86adc47893a8655bb3
Source dataset
uspto-grants-1993_03
Patent number
US05196570

Reaction notes

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