2-Methyl-5-(p-tolyl)-3-pentanol → 1,1,7-Trimethyl-1,2,3,4-tetrahydronaphthalene

HRID 915178

反応式

HRID 915178 の反応式
[CH3:1][CH:2]([CH:4](O)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)[CH3:3]>ClCCl>[CH3:1][C:2]1([CH3:3])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:13])[CH:11]=2)[CH2:6][CH2:5][CH2:4]1

参加物

3

反応物 1

HCID 617499612-Methyl-5-(p-tolyl)-3-pentanol

生成物 1

HCID 2263961,1,7-Trimethyl-1,2,3,4-tetrahydronaphthalene収率 99.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

A solution of 2-methyl-5-(p-tolyl)-3-pentanol (74 g, 0.385 mol) in dichloromethane (100 mL) was mixed with polyphosphoric acid (570 g) and the reaction mixture was heated to 60° C. and stirred overnight. After cooling, ice/water was slowly added and the aqueous extracted with dichloromethane. The organic layer was successively washed with water, aq NaHCO4, water and brine, dried (Mg2SO4), filtered and evaporated to give 67 g of 1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalene and used without further purification in the next step (step f). 1H NMR (300 MHz; CDCl3): 1.34 (s, 6 H), 1.69 (m, 2 H), 1.83 (m, 2 H), 2.37 (s, 3 H), 2.78 (m, 2 H), 6.99 (m, 2 H), 7.19 (s, 1 H).

後処理

  1. temperatureAfter cooling
  2. extractionthe aqueous extracted with dichloromethane
  3. washThe organic layer was successively washed with water, aq NaHCO4, water and brine
  4. dry with materialdried (Mg2SO4)
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-d3acbfcaa3714177bf120a6b757e0fab
出典データセット
uspto-grants-2007_09
特許番号
US07265139B2

関連ノート

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