Acetic Acid → HCID 86746097, compound

HRID 847361Notes

Reaction equation

HRID 847361 reaction equation
[CH2:1]1[C@@H:14]2[C@@:5]([C:15]([OH:17])=[O:16])([C:6]3[C:11]([CH2:12][CH2:13]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4][CH2:3][CH2:2]1.C(O)(=[O:20])C>O.[O-2].[O-2].[O-2].[Cr+6]>[O:20]=[C:12]1[CH2:13][C@H:14]2[C@:5]([C:15]([OH:17])=[O:16])([CH2:4][CH2:3][CH2:2][CH2:1]2)[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 2

HCID 176Acetic Acid2×HCID 13202691HCID 13202691, compound

Product 1

HCID 86746097HCID 86746097, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

A solution of the compound from Example 6 (42 g, 0.182 mol) in 900 mL glacial acetic acid was treated dropwise with a solution of chromium trioxide (91 g, 0.912 mol) in 850 mL of glacial acetic acid and 50 mL of water. The reaction was stirred at room temperature for 5 hours and concentrated. The residue was partitioned between benzene and water. The aqueous layer was saturated with NaCl and extracted with additional benzene. The combined organic layers were dried (MgSO4), filtered and concentrated to give a brown solid (37 g). The solid was suspended in 150 mL ethyl acetate and collected by suction filtration, and washed with additional ethyl acetate. The resulting material was dried under vacuum to give the title compound (21.0 g, 47%) as a white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between benzene and water
  3. extractionextracted with additional benzene
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ec516b0920c64f24b56b4a64edab827c
Source dataset
uspto-grants-1992_08
Patent number
US05141934

Reaction notes

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