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

HRID 484371

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To 18 ml of ice-cold concentrated H2SO4 was added 17.8 g (0.1 mol) of 2-methyl-5-phenyl-2-pentanol over 10 minutes. The mixture was then stirred at 0° C. for 15 minutes and at room temperature for 15 minutes. The mixture was treated with 50 ml of water and then extracted with ether. The ether extracts were combined and washed with water and saturated NaCl and NaHCO3 solutions and then dried (MgSO4). The solution was filtered and the solvent removed in-vacuo. The residue was purified by distillation (93° C.; 10 mm) to give the title compound as a colorless oil. PMR (CDCl3): δ 1.19 (6H, s), 1.45-1.53 (2H, m), 1.62-1.73 (2H, m), 2.62 (2H, t, J~6.1 Hz), 7.14-7.30 (4H, m).

Workup

extractionextracted with ether
washwashed with water and saturated NaCl and NaHCO3 solutions
dry with materialdried (MgSO4)
filtrationThe solution was filtered
customthe solvent removed in-vacuo
distillationThe residue was purified by distillation (93° C.; 10 mm)

Sources & evidence

ORD record: ord-623721c1bfeb4af2aa0bbf9e5ea52ef0
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05231113

Linked notes

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