Phosphorus oxide (P4O10) → 1,1-Dimethyl-1,2,3,4-tetrahydronaphthalene

HRID 613292

반응식

HRID 613292 반응식
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O[C:16]([CH3:27])([CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:17]>CS(O)(=O)=O>[CH3:17][C:16]1([CH3:27])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1

참가 물질

4

반응물 2

HCID 14812Phosphorus oxide (P4O10)HCID 3464292-Hydroxy-2-methyl-5-phenylpentane

생성물 1

HCID 161371,1-Dimethyl-1,2,3,4-tetrahydronaphthalene수율 90%

시약·촉매·용매 1

HCID 6395Methanesulfonic Acid용매

반응 조건

온도
105 °C

실험 절차

A mixture of P2O5 (55.3 g, 0.390 mol) in 400 ml of methanesulfonic acid was heated to 105° C. under argon until all of the solid had dissolved. The resulting solution was cooled to room temperature and 2-hydroxy-2-methyl-5-phenylpentane (63.0 g, 0.354 mol) added slowly with stirring. After 4 hours the reaction was quenched by carefully pouring the solution onto 1 L of ice. The resulting mixture was extracted with Et2O (4×125 ml)and the combined organic layers washed with water, saturated aqueous NaHCO3, water, and saturated aqueous NaCl before being dried over MgSO4. Concentration of the solution under reduced pressure, followed by distillation afforded 51.0 g (90%) of the product as a clear colorless oil, bp. 65-67° C./1.1 mmHg. 1H NMR (CDCl3): δ 7.32 (1H, d, J=7.4 Hz), 7.16-7.05 (3H, m), 2.77 (2H, t, J=6.3 Hz), 1.80 (2H, m), 1.66 (2H, m), 1.28 (6H, s).

후처리

  1. dissolutionhad dissolved
  2. temperatureThe resulting solution was cooled to room temperature
  3. customAfter 4 hours the reaction was quenched
  4. additionby carefully pouring the solution onto 1 L of ice
  5. extractionThe resulting mixture was extracted with Et2O (4×125 ml)
  6. washthe combined organic layers washed with water, saturated aqueous NaHCO3, water, and saturated aqueous NaCl
  7. dry with materialbefore being dried over MgSO4
  8. distillationConcentration of the solution under reduced pressure, followed by distillation

출처 및 근거

ORD 기록
ord-77ca0e0664644832bc1ab1258c26121b
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008204

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