Hydrochloric Acid → HCID 57581591, compound

HRID 2426118Notes

Reaction equation

HRID 2426118 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7]([C:12]2[O:16][N:15]=[C:14]([CH3:17])[N:13]=2)[CH:8]=[CH:9][C:10]=1[CH3:11].Cl>O1CCCC1.C(O)(C)C.O1CCOCC1>[CH3:11][C:10]1[CH:9]=[CH:8][C:7]([C:12]2[O:16][N:15]=[C:14]([CH3:17])[N:13]=2)=[CH:6][C:5]=1[OH:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 596497235-(3-Methoxymethoxy-4-methyl-phenyl)-3-methyl-[1,2,4]oxadiazole

Product 1

HCID 57581591HCID 57581591, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

To a solution of 5-(3-methoxymethoxy-4-methyl-phenyl)-3-methyl-[1,2,4]oxadiazole (1.23 g, 5.25 mmol) in tetrahydrofuran/isopropanol (1:1, 30 mL) was added 13.1 mL of 4M HCl in dioxane. The reaction mixture was stirred at room temperature for 18 hours. The solution was concentrated. The residue was diluted with ethyl acetate, washed with water and brine, dried (magnesium sulfate) and concentrated. The residue was recrystallized from ethyl acetate/hexane to afford 2-methyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenol. (Yield 0.88 g, 88%).

Workup

  1. concentrationThe solution was concentrated
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c9b2c9f008824fbbbae055a38219f58a
Source dataset
uspto-grants-2011_06
Patent number
US07968554B2

Reaction notes

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