2-[3-(Decyloxy)-4-(3-hydroxypropyl)phenoxy]benzoic acid ethyl ester → 2-(Decyloxy)-4-[2-(ethoxycarbonyl)phenoxy]benzenepropanoic acid ethyl ester

HRID 982448Notes

Reaction equation

HRID 982448 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][OH:21])=[C:14]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:13]=1)[CH3:2].[CH3:34][C:35](C)=O.[OH:38]S(O)(=O)=O.O=[Cr](=O)=O>CCOCC>[CH2:34]([O:21][C:20](=[O:38])[CH2:19][CH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([O:3][CH2:1][CH3:2])=[O:33])=[CH:13][C:14]=1[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH3:35]

Participants

4

Reactant 2

HCID 157180612-[3-(Decyloxy)-4-(3-hydroxypropyl)phenoxy]benzoic acid ethyl esterHCID 131709961Jones' reagent

Product 1

HCID 157180622-(Decyloxy)-4-[2-(ethoxycarbonyl)phenoxy]benzenepropanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 490 mg of 2-[3-(decyloxy)-4-(3-hydroxypropyl)phenoxy]benzoic acid ethyl ester in ether were added 1 ml of Jones reagent (chromic acid solution). After stirring for 1 hour, additional ether was added and the solution washed with a sodium bisulfite solution. The organic layer was dried and concentrated in vacuo. To the residue were added ethanol and a few drops of sulfuric acid. The mixture was refluxed overnight, cooled to room temperature, and concentrated in vacuo. Ethyl acetate was added and the organic solution washed with water. The organic layer was dried, concentrated in vacuo, and the residue purified by column chromatography eluting with 5% ethyl acetate in hexane. Combination concentration of the appropriate fractions yielded 110 mg of the desired subtitled intermediate as an oil. MS, IR, NMR.

Workup

  1. washthe solution washed with a sodium bisulfite solution
  2. customThe organic layer was dried
  3. concentrationconcentrated in vacuo
  4. additionTo the residue were added ethanol and a few drops of sulfuric acid
  5. temperatureThe mixture was refluxed overnight
  6. concentrationconcentrated in vacuo
  7. additionEthyl acetate was added
  8. washthe organic solution washed with water
  9. customThe organic layer was dried
  10. concentrationconcentrated in vacuo
  11. customthe residue purified by column chromatography
  12. washeluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-76414bedc758481d87561553b4490d51
Source dataset
uspto-grants-1991_02
Patent number
US04996230

Reaction notes

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