Isopropanol → HCID 14010395, compound

HRID 2119185Notes

Reaction equation

HRID 2119185 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-f07fff586b7742f3bde6c465d7b65d97
Source dataset
uspto-grants-1987_07
Patent number
US04683241

Reaction notes

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