Acetic Acid → HCID 10401638, compound

HRID 964496Notes

Reaction equation

HRID 964496 reaction equation
[CH3:1][C:2]1([CH3:20])[C:15]2[C:6](=[CH:7][C:8]3[C:9]([CH3:19])([CH3:18])[CH2:10][CH2:11][C:12]([CH3:17])([CH3:16])[C:13]=3[CH:14]=2)[CH2:5][CH2:4][CH2:3]1.CC(O)=[O:23]>[O-2].[O-2].[O-2].[Cr+6]>[CH3:1][C:2]1([CH3:20])[C:15]2[C:6](=[CH:7][C:8]3[C:9]([CH3:19])([CH3:18])[CH2:10][CH2:11][C:12]([CH3:17])([CH3:16])[C:13]=3[CH:14]=2)[C:5](=[O:23])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 10468381HCID 10468381, compound

Product 1

HCID 10401638HCID 10401638, compound

Reagents, catalysts & solvents 1

HCID 10219390chromium (VI) trioxideCatalyst

Procedure

A solution of chromium trioxide (13.55 mL of a 10% CrO3 /AcOH solution) was slowly added to a solution of finely ground 1,1,5,5,8,8-hexamethyl-1,2,3,4,5,6,7,8-octahydroanthracene (861 mg, 3.18 mmol) in AcOH (12 mL) at 25° C. The mixture was stirred for 30 min. Ice water (100 mL) was added, and the mixture was extracted with EtOAc (3×50 mL). The organic extracts were combined and twice treated with Et3N (10 mL), and washed and with sat. NaHCO3 (20 mL), water (2×20 mL) and brine (2×20 mL). The solvent was evaporated and the crude residue was purified by silica gel chromatography (hexanes:EtOAc 9:1) to give 831 mg of pure 3,4,5,6,7,8-hexahydro-4,4,5,5,8,8-hexamethyl-2H-anthracen-1-one (structure 1 where R1, R2, R3, and R4 are methyl, R5, R6, R7, R8, R9, and R10 are hydrogen, X and Y are carbon, Z is C(CH3)2 and m=n=1): 1H NMR (400 MHz, CDCl3) δ 7.97 (s, 1H, Ar), 7.31 (s, 1H, Ar), 2.68 (t, J=8.0 Hz, 2H), 1.98 (t, J=6.0 Hz, 2H), 1.68 (s, 4H) 1.37 (s, 3H), 1.30 (s, 3H), 1.29 (s, 3H). The above ketone was transformed to the title compound as outlined in Scheme II.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×50 mL)
  2. additiontwice treated with Et3N (10 mL)
  3. washwashed and with sat. NaHCO3 (20 mL), water (2×20 mL) and brine (2×20 mL)
  4. customThe solvent was evaporated
  5. customthe crude residue was purified by silica gel chromatography (hexanes:EtOAc 9:1)

Sources & evidence

ORD record
ord-862b1154d29c47429ea5812a4f33a5e7
Source dataset
uspto-grants-1998_06
Patent number
US05770378

Reaction notes

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