Sulfuric Acid → HCID 178424156, 화합물

HRID 986082노트

반응식

HRID 986082 반응식
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([Mg]Br)=[CH:3][CH:2]=1.[C:10]1([P:16]([O-])[O:17]CC)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.S(=O)(=O)(O)O>CCOCC>[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:13]1[CH:14]=[CH:15][C:10]([PH2:16]=[O:17])=[CH:11][CH:12]=1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 18981701ethoxy(phenyl)phosphiniteHCID 178418370HCID 178418370, 화합물

생성물 1

HCID 178424156HCID 178424156, 화합물수율 80.9%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A solution of p-tolylmagnesium bromide [prepared from p-bromotolueme (29.1 g, 0.16 mol) and magnesium (4.38 g, 0.18 g-atom)] in ether (100 mL) was treated with a solution of ethyl phenylphosphonite (13,6 g, 0.08 mol) in ether (50 mL) with vigorous mechanical stirring. The mixture was heated at reflux for 1/2 hr., then 100 mL of 25% sulfuric acid was added cautiously. Three layers formed; the bottom (aqueous) layer was extracted with toluene. Addition of NaHCO3, to the combined upper layers produced a vigorous reaction and a single organic phase. The organic phase was washed with water and with saturated NaCl, dried and evaporated to give an oil (14 g). Kugelrohr distillation at 120°-160° C. (0.1 mmHg) followed by chromatography on silica gel (CHCl3), then 10% MeOH-CHCl3) gave 7.1 g of an oil. This was distilled in the Kugelrohr again (150° C., 0.1 mmHg) to give 6.2 g of product which appears to be pure by NMR and crystallized on standing. 1H NMR (CDCl3) δ 8.0-7.2 (m, 9 H), 8.08 (d, J=480 Hz, 1 H), 2.42 (s, 3 H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1/2 hr
  3. customThree layers formed
  4. extractionthe bottom (aqueous) layer was extracted with toluene
  5. additionAddition of NaHCO3
  6. customto the combined upper layers produced
  7. customa vigorous reaction
  8. washThe organic phase was washed with water and with saturated NaCl
  9. customdried
  10. customevaporated

출처 및 근거

ORD 기록
ord-ac6035147242466d87525f35299c4f62
출처 데이터셋
uspto-grants-1987_12
특허 번호
US04710545

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