Sulfuric Acid → HCID 131728690, compound

HRID 1363644Notes

Reaction equation

HRID 1363644 reaction equation
[Br:1][C:2]1C(=O)[CH2:4][CH2:5][CH2:6][C:7]=1O.[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>[Br:1][C:2]1[C:7](=[N:27][OH:28])[CH2:6][CH2:5][CH2:4][C:10]=1[O:11][CH3:12]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 9005Trimethyl orthoformateHCID 159255Hydroxylamine, sulfate (1:1)HCID 516892Sodium BicarbonateHCID 2728340HCID 2728340, compound

Product 1

HCID 131728690HCID 131728690, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

2-Bromo-3-hydroxy-cylohex-2-enone (80.0 g, 420 mmol) is added to a mechanically stirred reactor followed by methanol (300 mL). To the mixture is then added trimethyl orthoformate (186 mL, 1.70 mol, 4 eq) and sulfuric acid (9 mL). The resulting mixture is stirred for 2 h until completion and hydroxylamine sulfate (34.4 g, 210 mmol, 0.5 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 (˜1100 g). The precipitate formed is collected by filtration (filter 10 cm diameter, 1.5 cm cake thickness, <1 min total filtration time) rinsed with heptane (200 mL) and dried under nitrogen flow for 4-6 h to provide 50.8 g, (55% yield) of 2-bromo-3-methoxy-cylohex-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, <1 min total filtration time)
  5. washrinsed with heptane (200 mL)
  6. customdried under nitrogen flow for 4-6 h

Sources & evidence

ORD record
ord-4df5652527384c58b96d5b3f4b874312
Source dataset
uspto-grants-2011_02
Patent number
US07884246B2

Reaction notes

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