Isopropanol → HCID 14010395, compound

HRID 2292197Notes

Reaction equation

HRID 2292197 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][C:18]=1[O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9].CC(C)=[O:28].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[C:2]([CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][C:18]=1[O:19][C:20](=[O:25])[C:21]([CH3:22])([CH3:24])[CH3:23])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])([OH:28])=[O:1]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14010392HCID 14010392, compoundHCID 131709961Jones' reagent

Product 1

HCID 14010395HCID 14010395, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1.01 g of 3-(hydroxypropyl)-4-pivaloyloxybenzophenone in 40 ml of acetone was treated with 1.5 ml of 8N Jones' Reagent at 0° C. for 1 h. The reaction mixture was treated with 5 ml of isopropyl alcohol and filtered to remove inorganic material. The filtrate was evaporated and the residue was taken up with toluene. The toluene phase was extracted with 3% KHCO3 solution and the aqeuous extract was acidified to pH 2. The acidic product was extracted with ethyl acetate. The ethyl acetate extact was washed with brine, dried (MgSO4), and concentrated to give 0.784 mg (74%) of product.

Workup

  1. filtrationfiltered
  2. customto remove inorganic material
  3. customThe filtrate was evaporated
  4. extractionThe toluene phase was extracted with 3% KHCO3 solution
  5. extractionthe aqeuous extract
  6. extractionThe acidic product was extracted with ethyl acetate
  7. washThe ethyl acetate extact was washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f47990c49e344fe9b86a92df3cdae7c6
Source dataset
uspto-grants-1989_01
Patent number
US04801610

Reaction notes

Loading…