Benzaldehyde → HCID 13118177, compound

HRID 1462848Notes

Reaction equation

HRID 1462848 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11].C([Li])CCC.CCCCCC.[CH:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1.CCOCC>[OH:33][CH:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 8058HexaneHCID 27340052,2,2'-TrimethylpropionanilideHCID 178418339Butyllithium2×

Product 1

HCID 13118177HCID 13118177, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of N-[(2-methyl)phenyl]-2,2-dimethyl-propanamide (95.6 g, 0.5 mol) in THF (500 ml) was cooled to 0° C. and treated with 1.6M n-butyllithium in hexane (628 ml, 0.1 mol). The addition of n-butyllithium was complete after 45 minutes. During the addition, the temperature of the mixture was maintained below 10° C. with external cooling. The resultant dianion solution was aged for 2 hours at 0° C. until the homogeneous orange solution became a yellow heterogeneous slurry. The dianion was then quenched with benzaldehyde (63.6 g, 0.6 mol) and aged for 15 minutes at about 24° C. The reaction mixture was diluted with ether (200 ml), treated with crushed ice (200 g), and stirred for 5 minutes. The organic phase was separated, washed with saturated sodium chloride (250 ml), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residual oil was crystallized from hexane, filtered and recrystallized from dichloromethane (500 ml reflux) to give N-[2-(2-hydroxy-2-phenylethyl)-phenyl]-2,2-dimethylpropanamide (87 g, 0.29 mol) in 58% yield. The product had a melting point of 183°-184° C.

Workup

  1. additionDuring the addition
  2. temperaturethe temperature of the mixture was maintained below 10° C. with external cooling
  3. waitThe resultant dianion solution was aged for 2 hours at 0° C. until the homogeneous orange solution
  4. waitaged for 15 minutes at about 24° C
  5. customThe organic phase was separated
  6. washwashed with saturated sodium chloride (250 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residual oil was crystallized from hexane
  11. filtrationfiltered
  12. customrecrystallized from dichloromethane (500 ml reflux)

Sources & evidence

ORD record
ord-becfdc9434784180a8eb7877988b37dc
Source dataset
uspto-grants-1984_07
Patent number
US04461728

Reaction notes

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