Acetamide, N-(3-methoxyphenyl)- → HCID 23312582, compound

HRID 745861Notes

Reaction equation

HRID 745861 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[O:8]C)(=[O:3])[CH3:2].[C:13](Cl)(=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:10]([C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17])=[C:7]([OH:8])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11494Acetamide, N-(3-methoxyphenyl)-HCID 61186Valeryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 23312582HCID 23312582, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The mixture consisting of 49.5 g of N-acetyl-m-anisidine, 72.3 cc of valeric acid chloride and 200 cc of methylene chloride is cooled to 0° C. 120 g of aluminum chloride are added little by little. The reaction mixture is refluxed for 2 hours with stirring, cooled, then poured in ice water. The resulting oily product is extracted with chloroform. The chloroform phase in turn is extracted with 2N sodium hydroxide solution which is then acidified. Thus, 24 g of 5-acetamido-2-valeryl phenol (MP 113° C.) are obtained.

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hours
  2. temperaturecooled
  3. extractionThe resulting oily product is extracted with chloroform
  4. extractionThe chloroform phase in turn is extracted with 2N sodium hydroxide solution which

Sources & evidence

ORD record
ord-63d91d739a6e4d36b1d64925c4313567
Source dataset
uspto-grants-1986_07
Patent number
US04600788

Reaction notes

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