Hydrochloric Acid → HCID 57581591, compound

HRID 2081108Notes

Reaction equation

HRID 2081108 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.CC(O)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-methyloxymethoxy-4-methyl-phenyl)-3-methyl-[1,2,4]oxadiazole (1.23 g, 5.25 mmol) (from Example 51 supra) in tetrahydrofuran/2-propanol (1:1, 30 mL) was added 13.1 mL of 4M HCl in dioxane (Aldrich). 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/hexanes and dried to give 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/hexanes
  7. customdried

Sources & evidence

ORD record
ord-e8743ebed8264a76adbef997919a0431
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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