Hydrochloric Acid → 2,3,6-TRIMETHYL-4-HYDROXYACETANILIDE

HRID 234268Notes

Reaction equation

HRID 234268 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 19078584HCID 19078584, compoundHCID 22281796Diisopropylether ethyl acetate

Product 1

HCID 232738462,3,6-TRIMETHYL-4-HYDROXYACETANILIDEYield 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 weakly acid and the resulting mixture was diluted with water. Crystals precipitated were filtered, washed with water, dried and then recrystallized from ethyl acetateisopropyl ether to obtain the desired compound (36.8 g, yield: 67.9%), m.p. 189°-190° C. (ethyl acetate-isopropyl ether).

Workup

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

Sources & evidence

ORD record
ord-7e652892357f4a89b5a5c5d010039648
Source dataset
uspto-grants-1997_01
Patent number
US05594154

Reaction notes

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