Acetic Acid → 2-(2,3,5-Trichlorophenyl)-4-methoxy-3-oxo-butyronitrile

HRID 234990Notes

Reaction equation

HRID 234990 reaction equation
[O-]CC.[Na+].[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=1[CH2:14][C:15]#[N:16].[CH3:17][O:18][CH2:19][C:20](OCC)=[O:21].C(O)(=O)C>C(O)C.COCCOC>[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=1[CH:14]([C:20](=[O:21])[CH2:19][O:18][CH3:17])[C:15]#[N:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 77544Ethyl 2-methoxyacetateHCID 2723922Sodium ethoxideHCID 197050992-(2,3,5-Trichlorophenyl)acetonitrile

Product 1

HCID 197050852-(2,3,5-Trichlorophenyl)-4-methoxy-3-oxo-butyronitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred refluxing solution of sodium ethoxide (from 1.38 g sodium) in ethanol (25 ml) was added over 5 minutes a mixture of 2,3,5-trichlorophenylacetonitrile (11 g) and ethyl methoxyacetate (8.85 g) in dry DME (25 ml). After 4 hours the mixture was cooled on ice and acidified by dropwise addition of acetic acid (ca. 6 ml), diluted with ice-water (150 ml) and extracted with dichloromethane (2×100 ml). The dichloromethane extract was washed with water, dried over MgSO4 and concentrated giving a yellow solid, which was triturated with a little ether and filtered. 8.6 g Homogeneous by TLC (19:1 CH2Cl2 :MeOH).

Workup

  1. additionwas added over 5 minutes
  2. temperatureAfter 4 hours the mixture was cooled on ice
  3. extractionextracted with dichloromethane (2×100 ml)
  4. extractionThe dichloromethane extract
  5. washwas washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customgiving a yellow solid, which
  9. customwas triturated with a little ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-9fa4a8710be14d8d9c7de45d87e7fe18
Source dataset
uspto-grants-1997_01
Patent number
US05597828

Reaction notes

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