Benzaldehyde → 2-Benzylidenecyclohexanone

HRID 1906429Notes

Reaction equation

HRID 1906429 reaction equation
N1(C2CCCCC=2)CC[O:4]CC1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>O>[C:14]1([CH:13]=[C:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]2=[O:4])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 241BenzeneHCID 313Hydrochloric AcidHCID 69589Morpholine, 4-(1-cyclohexen-1-yl)-

Product 1

HCID 989262-BenzylidenecyclohexanoneYield 96.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

According to the procedure of Birkofer, et al., Chem. Ber., 85, 1495 (1962), a mixture of 1-morpholinyl-1-cyclohexene (125.2 g. 0.75 mole), prepared as described above, benzaldehyde (53.1 g, 0.5 mole), and 200 ml of benzene was refluxed for 12 hours with azeotropic separation of 5.3 ml of water. The reaction mixture was cooled and treated with 300 ml of 6N aqueous hydrochloric acid and stirred at room temperature for one hour. The organic layer was separated, the aqueous layer was extracted with diethyl ether, and the combined organic layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. Distillation in vacuo (0.07 mm Hg) gave a fraction bp 124°-128° C., 61.1 g of the substitled product (96.2% pure by gas liquid chromatography (GLC) gas analysis). Crystallization from diethyl ether-petroleum ether (30°-60° C.) at -70° C. gave 47.7 g of the subtitled product, mp 48° -50° C. (100% pure by GLC; Birkhofer, et al., loc cit report mp 56° C.

Workup

  1. customprepared
  2. temperatureThe reaction mixture was cooled
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with diethyl ether
  5. washthe combined organic layer was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. distillationDistillation in vacuo (0.07 mm Hg)

Sources & evidence

ORD record
ord-782332f4142c419594404c55c91dc033
Source dataset
uspto-grants-1987_03
Patent number
US04652559

Reaction notes

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