Acetic Acid → 4-Acetamido-2,6-dimethylanisole

HRID 1488451

Reaction equation

HRID 1488451 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[C:4]([CH3:11])[CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].C(O)(=O)C.C(=O)(O)[O-].[Na+]>O>[C:12]([NH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[C:4]([CH3:11])[CH:3]=1)(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 41660974-Methoxy-3,5-dimethylaniline

Product 1

HCID 218527644-Acetamido-2,6-dimethylanisoleYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

4-Amino-2,6-dimethylanisole (4, 5 g, 33.2 mmol) was placed in a round-bottom flask fitted with a reflux condenser, and acetic anhydride (3.4 mL, 35.4 mmol) and acetic acid (3 mL, 53.1 mmol) were added sequentially. The mixture was heated to 50° C. for 4 h, cooled, poured into water and basified with saturated aq. sodium bicarbonate. The solution was extracted with methylene chloride, and the combined extracts were washed with brine and dried (MgSO4). Removing the solvent and recrystallizing the resulting solid from hexane-methylene chloride yielded 4-acetamido-2,6-dimethylanisole (7, 5.3 g, 83% yield). Spectral data: 1H NMR: δ 2.1 (s, 3H), 2.2 (s, 6H), 3.65 (s, 3H), 7.10 (s, 2H), 8.10 (s, 1H); 13C NMR: δ 16.1, 24.2, 60.0, 121.5, 131.8, 134.3, 154.3, 169.8; CI-HRMS: calcd. for C11H16NO2 (M+H+) 194.1181, fnd. 194.1181.

Workup

  1. customfitted with a reflux condenser
  2. temperaturecooled
  3. extractionThe solution was extracted with methylene chloride
  4. washthe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customRemoving the solvent
  7. customrecrystallizing the resulting solid from hexane-methylene chloride

Sources & evidence

ORD record
ord-71a403f3a8a64d90bf3e76cd93ce52c7
Source dataset
uspto-grants-1997_10
Patent number
US05674876

Linked notes

Loading…