Diethyl Ether → p-Benzyloxycinnamaldehyde

HRID 1282924Notes

Reaction equation

HRID 1282924 reaction equation
C(NC(C)C)(C)C.C(=NC1CCCCC1)C.[CH2:17]([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:33]([O:35]CC)[CH3:34]>C([Li])CCC.CCCCCC.O1CCCC1>[CH2:17]([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[CH:34][CH:33]=[O:35])=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 3283Diethyl Ether3×HCID 7912DiisopropylamineHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 10964544N-cyclohexylethanimine

Product 1

HCID 54136827p-Benzyloxycinnamaldehyde

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 178418339ButyllithiumSolvent

Procedure

Other N-methyl-cinnamylamines can be prepared as follows: To the solution of 5.55 g of di-isopropylamine in 60 ml of diethyl ether, 35 ml of 1.6 molar n-butyl lithium in hexane are added dropwise while stirring at -20° under nitrogen. Thereupon the solution of 6.9 g of N-ethylidenecyclohexylamine in 50 ml of diethyl ether is added dropwise at -20°, followed by the solution of 10.6 g of 4-benzyloxy-benzaldehyde in 50 ml of diethyl ether and 10 ml of tetrahydrofuran at -70°. The mixture is stirred for 1 hour at room temperature, washed with 50 ml of water and stirred with 100 ml of water and 50 ml of acetic acid for 8 hours at room temperature. The ethereal layer is collected, washed with water, N hydrochloric acid, 2N aqueous sodium hydroxide and saturated aqueous sodium chloride, dried and evaporated, to yield the 4-benzyloxycinnamaldehyde.

Workup

  1. stirringThe mixture is stirred for 1 hour at room temperature
  2. washwashed with 50 ml of water
  3. stirringstirred with 100 ml of water and 50 ml of acetic acid for 8 hours at room temperature
  4. customThe ethereal layer is collected
  5. washwashed with water, N hydrochloric acid, 2N aqueous sodium hydroxide and saturated aqueous sodium chloride
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-ac4391a58c504291822ce0cfdaa78976
Source dataset
uspto-grants-1976_08
Patent number
US03973030

Reaction notes

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