Water → HCID 14451560, compound

HRID 1666296Notes

Reaction equation

HRID 1666296 reaction equation
[C-:1]#[N:2].[K+].O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16])[CH:10]=[O:11].[C:19]([O:22]C(=O)C)(=O)[CH3:20]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.ClCCl>[CH3:18][O:17][C:13]1[CH:12]=[C:9]([CH:10]([O:11][C:19](=[O:22])[CH3:20])[C:1]#[N:2])[CH:8]=[C:7]([O:6][CH3:5])[C:14]=1[O:15][CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 68583,4,5-TrimethoxybenzaldehydeHCID 7918Acetic AnhydrideHCID 9032Potassium Cyanide

Product 1

HCID 14451560HCID 14451560, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of potassium cyanide (41.5 g), triethylbenzylammonium chloride (5.23 g), water (130 ml) and dichloromethane (150 ml) was cooled to 0° C. To the vigorously stirred mixture, a solution containing the 3,4,5-trimethoxy-benzaldehyde (100.0 g) and acetic anhydride (52.1 g) in dichloromethane (150 ml) was added drop wise at 0° C. during 30 minutes. The stirring was continued at 0° C. for 30 minutes and then at ambient temperature for one hour. The organic phase was separated, dried and concentrated to dryness, leaving crude 3,4,5-trimethoxyphenyl-α-acetoxyacetonitrile. Crystallization from ethanol-water afforded the pure product (104 g), m.p. 65-66° C.

Workup

  1. additionwas added drop wise at 0° C. during 30 minutes
  2. waitat ambient temperature for one hour
  3. customThe organic phase was separated
  4. customdried
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0174de7a3e60410da03caa587d376b01
Source dataset
uspto-grants-2011_10
Patent number
US08044067B2

Reaction notes

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