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

HRID 613292

反応式

HRID 613292 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 161371,1-Dimethyl-1,2,3,4-tetrahydronaphthalene収率 90%

試薬・触媒・溶媒 1

HCID 6395Methanesulfonic Acid溶媒

反応条件

温度
105 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-77ca0e0664644832bc1ab1258c26121b
出典データセット
uspto-grants-1999_12
特許番号
US06008204

関連ノート

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