Acetic Acid → 3-Methyl-4-(morpholin-4-yl)benzoic acid

HRID 1954794Notes

Reaction equation

HRID 1954794 reaction equation
[CH3:1][C:2]1[CH:3]=C([CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)C#N.Cl.[C:17]([OH:20])(=[O:19])[CH3:18]>>[CH3:3][C:2]1[CH:1]=[C:18]([CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[C:17]([OH:20])=[O:19]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 18475738HCID 18475738, compound

Product 1

HCID 184757233-Methyl-4-(morpholin-4-yl)benzoic acidYield 91%

Procedure

To a solution of 3-methyl-4-morpholinobenzonitrile (1.0 g, 4.9 mmol) in glacial acetic acid (10 mL) was added a 20% aqueous hydrochloric acid solution (60 mL) and the reaction was heated at reflux for 35 h. The acetic acid was evaporated in vacuo and the remaining water solution was alkalized with 2 M aqueous sodium hydroxide solution to pH 8. The solution was washed, twice, with chloroform and the water phase was adjusted to pH 4 with a 2 M aqueous hydrochloric acid solution. The product was filtered off and dried in vacuo to afford 1.0 g (91% yield) of the title compound as white crystals: mp 220-221° C.; EIMS (70 eV) m/z (relative intensity) 221 (100, M+).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 35 h
  3. customThe acetic acid was evaporated in vacuo
  4. washThe solution was washed
  5. filtrationThe product was filtered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-fa6f99eb4edd4e5ea9580b56608eb808
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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