2-Hydroxy-2-methyl-5-phenylpentane → 1,1-Dimethyl-1,2,3,4-tetrahydronaphthalene

HRID 495897

Reaction equation

O[C:2]([CH3:13])([CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:3]>CS(O)(=O)=O>[CH3:3][C:2]1([CH3:13])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of P2O, (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).

Workup

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

Sources & evidence

ORD record: ord-d9c5440c33df48a89c439d1e9e92af16
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06942980B1

Linked notes

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