Hydrochloric Acid → 4-Acetylamino-2,3,5-trimethylphenol

HRID 1493059Notes

Reaction equation

HRID 1493059 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([NH:18][C:19](=[O:21])[CH3:20])=[C:13]([CH3:22])[C:12]=1[CH3:23])(=O)C.Cl.C(OCC)(=O)C.C(OC(C)C)(C)C>O.CO>[C:19]([NH:18][C:14]1[C:15]([CH3:17])=[CH:16][C:11]([OH:10])=[C:12]([CH3:23])[C:13]=1[CH3:22])(=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 190785841-Acetoxy-4-acetylamino-2,3,5-trimethylbenzeneHCID 22281796Diisopropylether ethyl acetate

Product 1

HCID 232738464-Acetylamino-2,3,5-trimethylphenolYield 67.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of potassium carbonate (27 g, 195 mmol) in water (150 ml) was added to a solution of 1-acetoxy-4-acetylamino-2,3,5-trimethylbenzene (66.0 g, 324 mmol) in methanol (300 ml) and the mixture was stirred for 1 hour under an argon atmosphere. Aqueous 1N hydrochloric acid solution was added to the reaction mixture to make the mixture weak by acid and the resulting mixture was diluted with water. Crystals precipitated were filtered, washed with water, dried and then recrystallized from ethyl acetate-isopropyl ether to obtain the desired compound (36.8 g, yield: 67.9%), m.p. 189°-190° C. (ethyl acetate-isopropyl ether). NMR (DMSO-d6) δ 1.98 (3H, s), 1.99 (6H, s) , 2.01 (3H, s), 6.50 (1H, s), 8.95 (1H, s), 9.00 (1H, s).

Workup

  1. customCrystals precipitated
  2. filtrationwere filtered
  3. washwashed with water
  4. customdried
  5. customrecrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-ed7a5a62bfe04027b3e4122744e1c6f4
Source dataset
uspto-grants-1994_12
Patent number
US05376681

Reaction notes

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