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

HRID 915178

Reaction equation

HRID 915178 reaction equation
[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

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d3acbfcaa3714177bf120a6b757e0fab
Source dataset
uspto-grants-2007_09
Patent number
US07265139B2

Linked notes

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