Diethyl Ether →

HRID 620757Notes

Reaction equation

HRID 620757 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][C:5]=1[O:13][CH3:14])[CH3:2].[C:15](OC(=O)C)(=[O:17])[CH3:16].[Cl:22]([OH:26])(=[O:25])(=[O:24])=[O:23].[CH2:27]([O:29]CC)[CH3:28]>>[Cl:22]([O-:26])(=[O:25])(=[O:24])=[O:23].[C:15]([NH:12][C:11]1[O:29][CH2+:27]([CH3:28])[C:8]2[CH:9]=[C:4]([O:3][CH2:1][CH3:2])[C:5]([O:13][CH3:14])=[CH:6][C:7]=2[CH:10]=1)(=[O:17])[CH3:16]

Participants

4

Reactant 4

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 24247Perchloric AcidHCID 38639514-Ethoxy-3-Methoxyphenylacetonitrile

Product 0

No Product data yet.

Procedure

To an ice-cooled and stirred solution of 25 grams 4-ethoxy-3-methoxyphenylacetonitrile (0.13 mmol) in 74 ml acetic anhydride (0.785 mol) was slowly added perchloric acid (70%, 11.7 N, 15.5 ml, 0.182 mol) over a 15 minute period. The dark reaction mixture slowly became a yellow slurry and was stirred at room temperature for 42 hours. The mixture was diluted with 200 ml diethyl ether and a crystalline yellow solid was isolated by filtration, washed with diethyl ether and dried in vacuo to provide 47.3 grams of Compound 8d (100% yield) having a melting point of 188°-189° C. (with decomposition).

Workup

  1. customover a 15 minute
  2. customThe dark reaction mixture
  3. customa crystalline yellow solid was isolated by filtration
  4. washwashed with diethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ff4e33adafad47d1a4a2746b694a7fab
Source dataset
uspto-grants-1989_04
Patent number
US04822800

Reaction notes

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