Water → 3'-Benzyloxy-2-methylbenzanilide

HRID 1287696Notes

Reaction equation

HRID 1287696 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13].[OH-].[K+].[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>C(O)C>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 14797Potassium HydroxideHCID 11401898Benzamide, N-(3-hydroxyphenyl)-2-methyl-

Product 1

HCID 170859693'-Benzyloxy-2-methylbenzanilideYield 60.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 9.1 g (0.04 mol) portion of 3'-hydroxy-2-methylbenzanilide was dissolved in a solution of 2.3 g (0.041 mol) of potassium hydroxide in 50 ml of ethanol, and 5.1 g (0.04 mol) of benzylchloride was added dropwise to the above solution with stirring at room temperature. After the addition, the reaction mixture was warmed and refluxed for 3 hours. The reaction mixture was poured into 200 ml of water and the precipitated product was filtered and washed with water and dried. The product was recrystallized from 90% methanol to obtain 7.5 g (60.5%) of white needles having a melting point of 114°-115° C.

Workup

  1. additionwas added dropwise to the above solution
  2. additionAfter the addition
  3. temperaturethe reaction mixture was warmed
  4. temperaturerefluxed for 3 hours
  5. filtrationthe precipitated product was filtered
  6. washwashed with water
  7. customdried
  8. customThe product was recrystallized from 90% methanol

Sources & evidence

ORD record
ord-2fb9b66bbf204e6eb8a4ea3c62e2601d
Source dataset
uspto-grants-1976_10
Patent number
US03985804

Reaction notes

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