Sulfuric Acid → HCID 15070140, compound

HRID 2081318Notes

Reaction equation

HRID 2081318 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[CH:15]=[CH:16]/[CH:17]=[CH:18]/[CH:19]([OH:28])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])C.[OH-].[Na+].S(=O)(=O)(O)O.C(OCC)(=O)C>CO>[OH:28][CH:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])/[CH:18]=[CH:17]/[CH:16]=[CH:15]/[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:29])=[O:3]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 15070124HCID 15070124, compound

Product 1

HCID 15070140HCID 15070140, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 130 mg of 4-[2-[(1E,3E)-(5RS)-5-hydroxy-1,3-tridecadienyl]-phenoxy]butyric acid ethyl ester in 10 ml of methanol and 2.5 ml of 0.5 n sodium hydroxide solution is stirred under argon atmosphere for 3 hours at room temperature. The reaction mixture is poured on ice water, acidified to pH 5 with 0.5 n sulfuric acid and shaken out with ethyl acetate. The organic phase is dried, concentrated by evaporation and the residue is chromatographed on silica gel with n-hexane/diethyl ether=7/3. 78 mg of the title compound is obtained as a colorless oil.

Workup

  1. additionThe reaction mixture is poured on ice water
  2. customThe organic phase is dried
  3. concentrationconcentrated by evaporation
  4. customthe residue is chromatographed on silica gel with n-hexane/diethyl ether=7/3

Sources & evidence

ORD record
ord-05cdfdcface241c990fc4a2d9685b4a9
Source dataset
uspto-grants-1993_02
Patent number
US05183925

Reaction notes

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