Water → HCID 22758859, compound

HRID 1704807Notes

Reaction equation

HRID 1704807 reaction equation
[CH2:1]([CH:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[C:5]#[N:6])[CH:2]=[CH2:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[CH2:1]([CH:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[CH2:5][NH2:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 10750085HCID 10750085, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 22758859HCID 22758859, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of (±)-2-allyl-2-(4-methoxyphenyl)acetonitrile (159.7 g., 0.852 mole) in diethyl ether (200 ml.) was added dropwise during 20 minutes to a stirred, slowly refluxing mixture of lithium aluminum hydride (LiAlH4, 42.2 g., 1.11 moles) in diethyl ether (800 ml.). The mixture was refluxed for an additional 1.25 hours and then cooled in an ice-H2O bath. The excess LiAlH4 was decomposed by the slow dropwise addition of H2O until gaseous evolution ceased, and a granular precipitate formed. The mixture was filtered and the filter cake thoroughly washed with diethyl ether. Concentration of the filtrate gave the title product (146 g., 90%) as a cloudy oil.

Workup

  1. temperatureslowly refluxing
  2. temperatureThe mixture was refluxed for an additional 1.25 hours
  3. temperaturecooled in an ice-H2O bath
  4. customa granular precipitate formed
  5. filtrationThe mixture was filtered
  6. washthe filter cake thoroughly washed with diethyl ether

Sources & evidence

ORD record
ord-f1569b425ff049bf81a4315d3e7ee3ce
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

Loading…