Benzophenone → HCID 23436665, compound

HRID 2120938Notes

Reaction equation

HRID 2120938 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 46.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 500 mL round bottom flask containing 2-adamantylcyclopentadiene (30.18 g, 150.7 mmol) was added benzophenone (27.50 g, 150.9 mmol) and 300 mL absolute ethanol. Once the solids had dissolved, sodium methoxide (15.00 g, 278 mmol) was added and the reaction was stirred for six days. The orange precipitate was collected by suction filtration and the air dried product was then stirred in 100 methanol for two days before the solid was collected by suction filtration and washed with 100 mL methanol. Drying in vacuo for two days provided 25.72 grams of desired product (46.8%). And second crop was obtained: 6.08 grams (57.9% for both crops). MS (GC-MS) m/z 364.5 (M+). 1H NMR (CDCl3): δ 1.52-2.23 (m, 14H, adamantyl-H), 2.80 (s, 1H, 2-H-adamantyl), 7.30-7.40 (m, 12H, phenyl-H), 6.05 (m, 1H, fulvene-H), 6.29, 6.59 (d, 3JHH=3.4, 3.7 Hz, 2H, fulvene-H). 13C NMR (CDCl3): δ 28.14, 28.14, 31.21, 31.21, 32.72, 32.72, 38.06, 38.92, 38.92 (adamantyl-C), 45.20 (2-C-adamantyl), 118.16, 125.01, 133.10 (fulvene-CH1), 127.68, 127.68, 127.77, 127.77, 128.31, 128.31, 132.02, 132.02, 132.08, 132.08 (phenyl-CH1), 141.70, 141.70 (ipso-C), 144.39, 148.69, 152.27 (fulvene-CH0). Elemental analysis calculated for C28H28: C, 92.26; H, 7.74. Found: C, 83.42; H, 6.59.

Workup

  1. dissolutionOnce the solids had dissolved
  2. filtrationThe orange precipitate was collected by suction filtration
  3. stirringthe air dried product was then stirred in 100 methanol for two days before the solid
  4. filtrationwas collected by suction filtration
  5. washwashed with 100 mL methanol
  6. customDrying in vacuo for two days

Sources & evidence

ORD record
ord-cd218685ca1e4de79fc71ca55b37ecab
Source dataset
uspto-grants-2004_02
Patent number
US06693153B2

Reaction notes

Loading…