Benzophenone → HCID 23436665, compound

HRID 2120949Notes

Reaction equation

HRID 2120949 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%).

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-9c98317cf61f4c5fa690d6ce4f2afb19
Source dataset
uspto-grants-2004_02
Patent number
US06693153B2

Reaction notes

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