Methanol → HCID 53679807, compound

HRID 846250Notes

Reaction equation

HRID 846250 reaction equation
[CH2:1]([CH:3]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)[CH3:2].[C:18]1([CH2:24][C:25]#[N:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CO.[OH-].[Na+]>O>[CH2:1]([CH:3]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[C:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:25]#[N:26])=[CH:8][CH:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8794PhenylacetonitrileHCID 14798Sodium HydroxideHCID 14997927HCID 14997927, compound

Product 1

HCID 53679807HCID 53679807, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

70.2 Grams of 4-[(2-ethylhexyl)oxy]benzaldehyde (prepared as described in the preceding paragraph) and 38.6 g of phenylacetonitrile were added to 800 ml of methanol and stirred cold (10°-15° C.). To this was added (dropwise) 125 ml of aqueous sodium hydroxide (50 percent) with continued stirring at 10°-15° C. for an additional two hours. The mixture was then stirred overnight at room temperature and then poured into cold water and extracted with ethyl acetate. The extract was dried and evaporated to yield α-[[4-(2-ethylhexyloxy)phenyl]methylene]benzeneacetonitrile which was catalytically reduced as follows.

Workup

  1. stirringwith continued stirring at 10°-15° C. for an additional two hours
  2. stirringThe mixture was then stirred overnight at room temperature
  3. extractionextracted with ethyl acetate
  4. customThe extract was dried
  5. customevaporated

Sources & evidence

ORD record
ord-d38db798624445e389840e62b89e7a93
Source dataset
uspto-grants-1992_08
Patent number
US05135955

Reaction notes

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