Benzophenone → HCID 23436665, compound

HRID 2120937Notes

Reaction equation

HRID 2120937 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[C:11]1[CH2:15][CH:14]=[CH:13][CH:12]=1)[CH2:8]2.[C:16]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C[O-].[Na+]>C(O)C>[CH:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH:2]1[C:11]1[CH:15]=[CH:14][C:13](=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:12]=1)[CH2:10]2

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 10942334Sodium MethoxideHCID 23436668HCID 23436668, compound

Product 1

HCID 23436665HCID 23436665, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 250 mL round bottom flask was charged with 2-adamantylcyclopentadiene (10.24 g, 51.13 mmol), benzophenone (9.32 g, 51.13 mmol) and 100 mL absolute ethanol. Once the solids had dissolved, sodium methoxide (5.00 g, 92.6 mmol) was added and the reaction was stirred for five days. The orange precipitate was collected by suction filtration and washed with 50 mL ethanol. The air dried product was stirred in 100 methanol overnight and the solid was collected by suction filtration and washed with 50 mL methanol. Drying in vacuo for several hours provided 13.32 grams of desired product (71.5%). MS (GC-MS) m/z 364.5 (M+). Elemental analysis calculated for C28H28: C, 92.26; H, 7.74. Found: C, 87.05; H, 6.92.

Workup

  1. dissolutionOnce the solids had dissolved
  2. filtrationThe orange precipitate was collected by suction filtration
  3. washwashed with 50 mL ethanol
  4. stirringThe air dried product was stirred in 100 methanol overnight
  5. filtrationthe solid was collected by suction filtration
  6. washwashed with 50 mL methanol
  7. customDrying in vacuo for several hours

Sources & evidence

ORD record
ord-35b8faa3f5a34c05a7fc068d302c4d97
Source dataset
uspto-grants-2004_02
Patent number
US06693153B2

Reaction notes

Loading…