Sulfuric Acid → HCID 53896293、化合物

HRID 2389513ノート

反応式

HRID 2389513 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 53896293HCID 53896293、化合物

試薬・触媒・溶媒 3

HCID 23665763Sodium Bisulfite触媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
70 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-651359850f86458287f030e93d4735ce
出典データセット
uspto-grants-2012_09
特許番号
US08273740B2

反応ノート

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