Sulfuric Acid → HCID 86625062, compound

HRID 1363645Notes

Reaction equation

HRID 1363645 reaction equation
O[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=O)[C:3]=1C.[CH:10](OC)(OC)[O:11][CH3:12].S(=O)(=O)(O)O.S(O)(O)(=O)=O.[NH2:27][OH:28].C(=O)(O)[O-].[Na+]>CO>[CH3:12][O:11][C:10]1[CH2:6][CH2:5][CH2:4][C:3](=[N:27][OH:28])[C:2]=1[CH3:7]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 9005Trimethyl orthoformateHCID 159255Hydroxylamine, sulfate (1:1)HCID 516892Sodium BicarbonateHCID 70579622-Cyclohexen-1-one, 3-hydroxy-2-methyl-

Product 1

HCID 86625062HCID 86625062, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

3-Hydroxy-2-methyl-cyclohex-2-enone (500 g, 3.96 mol) is added to a mechanically stirred reactor. To this is added methanol (1.35 L) followed by trimethyl orthoformate (1.65 L, 15.85 mol, 4 eq) and sulfuric acid (15 mL). The resulting mixture is stirred for 2 h until completion and hydroxylamine sulfate (275 g, 3.96 mol, 1 eq) is added as a solid. The mixture is heated to 40° C. and stirred at that temperature until complete conversion (2-2.5 h). The solution is then cooled to 5° C. and the pH is adjusted to 7 with saturated sodium bicarbonate (˜3 L). The precipitate formed is collected by filtration (filter 10 cm diameter, 1.5 cm cake thickness, <3 min total filtration time), rinsed with heptane (400 mL) and dried under nitrogen flow for 4-6 h to provide 560 g (92% yield) of 3-methoxy-2-methyl-cyclohex-2-enone oxime.

Workup

  1. additionis added as a solid
  2. temperatureThe solution is then cooled to 5° C.
  3. customThe precipitate formed
  4. filtrationis collected by filtration (filter 10 cm diameter, 1.5 cm cake thickness, <3 min total filtration time)
  5. washrinsed with heptane (400 mL)
  6. customdried under nitrogen flow for 4-6 h

Sources & evidence

ORD record
ord-9456b066809e437e823fb1b122d0dc55
Source dataset
uspto-grants-2011_02
Patent number
US07884246B2

Reaction notes

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