Sulfuric Acid → HCID 53896293, compound

HRID 2389513Notes

Reaction equation

HRID 2389513 reaction equation
[C:1]([O-:4])([O-])=[O:2].[K+].[K+].[OH-].[K+].Cl[CH2:10][C:11]1[CH:12]=[C:13](C(=O)C)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].S(=O)(=O)(O)[OH:23]>O.O1CCOCC1.OS([O-])=O.[Na+]>[OH:23][CH2:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:1]([OH:4])=[O:2]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 27767231-[3-(Chloromethyl)-4-methoxyphenyl]ethan-1-one

Product 1

HCID 53896293HCID 53896293, compound

Reagents, catalysts & solvents 3

HCID 23665763Sodium BisulfiteCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Onto a warm solution of Ca(OCl)2 (7.14 g, 49.95 mmol, 3.3 eq.) in water (25 ml) is added a warm solution of K2CO3 (5.14 g, 37.35 mmol, 2.49 eq.) and KOH (1.46 g, 26.1 mmol, 1.74 eq.) in water (25 ml). After 30 min of vigourous stirring, the undesired solid formed is filtered and rinsed with little water. The solution obtained is poured onto a suspension of 1-(3-chloromethyl-4-methoxy-phenyl)-ethanone (2.98 g, 15 mmol) in 1,4-dioxane (10 ml). The resulting suspension is stirred 2 h at rt and 2 h at 70° C. Under cooling of the suspension in an ice bath, are subsequently added solid NaHSO3 (100 mg), then 96% sulfuric acid until pH=3. The aqueous phase thus obtained is extracted four times with AcOEt. The combined organic phase is washed with brine and dried over Na2SO4. Evaporation of the solvent in vacuo yields the title compound (1.8 g) in 66% as a white solid. tR=0.72 min (LC-3), ESI-MS (pos.): m/z 182.99 [M+H]+.

Workup

  1. customthe undesired solid formed
  2. filtrationis filtered
  3. washrinsed with little water
  4. customThe solution obtained
  5. temperatureUnder cooling of the suspension in an ice bath
  6. customThe aqueous phase thus obtained
  7. extractionis extracted four times with AcOEt
  8. washThe combined organic phase is washed with brine
  9. dry with materialdried over Na2SO4
  10. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-651359850f86458287f030e93d4735ce
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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