Cumene → HCID 10536243, compound

HRID 1929248Notes

Reaction equation

HRID 1929248 reaction equation
C1CCCCC1.C1(C(C)C)C=CC=CC=1.[CH3:16][NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([Li])CCC.[CH:29]12[O:35][CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34]2>>[CH3:16][N:17]([C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]1[OH:35])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 5

HCID 7406CumeneHCID 7515N-MethylanilineHCID 8078CyclohexaneHCID 9246Cyclohexene oxideHCID 178418339Butyllithium

Product 1

HCID 10536243HCID 10536243, compoundYield 75%

Procedure

To a 500 mL round bottom flask was added 100 mL of 1.2 M potassium t-amylate in cyclohexane (0.12 moles) and 41.7 mL of cumene (0.3 moles) under a constant flow of nitrogen gas. Then 10.8 mL of N-methylaniline (0.1 moles) was added to the reaction mixture while the reaction was continuously stirred. n-Butyllithium (46 mL of a 2.2 M solution, 0.1 moles) was added and the resulting amide was left stirring for two days. Cyclohexene oxide (10.1 mL, 0.1 moles) was added. After 24 hours, the reaction was quenched by carefully adding water under the flow of nitrogen. Washing of the product with 100 mL of distilled water yielded two layers of which the organic layer was extracted. Repeated rotovapor distillations removed most of the cumene. Any leftover cumene after rotovapor distillation was removed by vacuum horizontal distillation. This device employs a vacuum (<1 mm Hg) and liquid nitrogen to trap cumene, which distilled at about 85° C., but 16 g of racemic MPAC (0.075 moles, 75% yield) distilled at 120° C. The product, MPAC, was analyzed by NMR spectroscopy and the spectrum confirmed the presence of the compound when it was compared to that of literature (Swamy and Raghavendra, 2002).

Workup

  1. stirringstirring for two days
  2. customthe reaction was quenched by carefully adding water under the flow of nitrogen
  3. washWashing of the product with 100 mL of distilled water
  4. customyielded two layers of which the organic layer
  5. extractionwas extracted
  6. customremoved most of the cumene
  7. distillationAny leftover cumene after rotovapor distillation
  8. customwas removed by vacuum horizontal distillation
  9. distillationdistilled at about 85° C.

Sources & evidence

ORD record
ord-da4d441e76d14a35b6474a04ec7e2c58
Source dataset
uspto-grants-2012_05
Patent number
US08187468B2

Reaction notes

Loading…