HCID 12851639, compound → HCID 13753870, compound

HRID 652504Notes

Reaction equation

HRID 652504 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:5]=[CH:4][C:3]=1[C:16](=[O:18])[CH3:17].CC(C)=[O:21].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:16]([C:3]1[CH:4]=[CH:5][C:6]([O:11][CH2:12][CH2:13][C:14]([OH:21])=[O:15])=[C:7]([CH2:8][CH2:9][CH3:10])[C:2]=1[OH:1])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 12851639HCID 12851639, compoundHCID 131709961Jones' reagent

Product 1

HCID 13753870HCID 13753870, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 2.00 g of 1-[2-hydroxy-4-(3-hydroxy-propoxy)-3-propylphenyl]ethanone in 30 ml of acetone was added dropwise over 45 minutes to a stirred, ice cooled solution of 4.0 ml of Jones reagent in 10 ml of acetone. After 15 additional minutes, the cooling bath was removed and the reaction mixture was stirred at 23° for 15 minutes. Jones reagent (0.5 ml) was added and stirring was continued for 15 minutes. The reaction mixture was concentrated in vacuo and the residue was treated with water and extracted with ether. The ether extract was washed with three portions of 1N sodium hydroxide and the aqueous layers were combined and acidified. The product was extracted with ether and the dried (over magnesium sulfate) extract was concentrated in vacuo to a solid (1.48 g). Recrystallization from ether-hexane gave 1.21 g, mp 142°-146°, (57% yield) of 3-(4-acetyl-3hydroxy-2-propylphenoxy)propanoic acid, the titled compound.

Workup

  1. customAfter 15 additional minutes, the cooling bath was removed
  2. additionJones reagent (0.5 ml) was added
  3. stirringstirring
  4. waitwas continued for 15 minutes
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. additionthe residue was treated with water
  7. extractionextracted with ether
  8. extractionThe ether extract
  9. washwas washed with three portions of 1N sodium hydroxide
  10. extractionThe product was extracted with ether
  11. dry with materialthe dried (over magnesium sulfate)
  12. extractionextract
  13. concentrationwas concentrated in vacuo to a solid (1.48 g)
  14. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-bb4b8001a6894060aac56ca73399d3b0
Source dataset
uspto-grants-1987_06
Patent number
US04672066

Reaction notes

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