Benzophenone → Nonanal

HRID 1287658Notes

Reaction equation

HRID 1287658 reaction equation
[Na].[C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)[C:3]1C=CC=C[CH:4]=1.C1C[O:19]CC1>CCCCCC>[CH:4](=[O:19])[CH2:3][CH2:2][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 8028TetrahydrofuranHCID 5360545Sodium

Product 1

HCID 31289NonanalYield 92%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Using a Fisher-Porter bottle, 0.86 g (37.4 mmol) of solid sodium metal and 2.91 g (16 mmol) of benzophenone were added to 40 ml of dry, degassed THF under N2 flow. The reaction turned blue, characteristic of the ketyl. The Fisher-Porter bottle was then pressured up to 43 psi over atmospheric with CO and the whole reaction stirred vigorously using a magnetic stirrer at 120°. At this pressure THF can reach temperatures in excess of 100° before boiling. The reaction was cooled to 60° and 2.25 ml (16.8 mmol) of Fe(CO)5 was added. A white precipitate remained after addition of n-hexane. Washing the white precipitate and pumping to dryness gave a product that yielded 92% nonanal based on 214 MW for Na2Fe(CO)4. The product of this example was not solvated.

Workup

  1. additionwere added to 40 ml
  2. customof dry
  3. customdegassed THF under N2 flow
  4. customthe whole reaction
  5. customat 120°
  6. customexcess of 100°
  7. temperatureThe reaction was cooled to 60°
  8. washWashing the white precipitate
  9. customgave a product that

Sources & evidence

ORD record
ord-f04489fc17764ef2a0c366f862dcacf0
Source dataset
uspto-grants-1976_10
Patent number
US03985770

Reaction notes

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