Sulfuric Acid → 1,1,7-Trimethyl-1,2,3,4-tetrahydronaphthalene

HRID 51160

Reaction equation

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

Conditions

Temperature: 0 °C

Procedure

A solution of 2-methyl-5-(p-tolyl)-pentan-2-ol (10.4 g, 54.1 mmol) in ethyl ether (100 mL) at 0° C. was treated with concentrated sulfuric acid (64 mL). The mixture was stirred at 0° C. for 1.5 hours, and then poured into a mixture of ice/water. The mixture was diluted with ethyl ether, the organic phase was separated, washed with water (2×), saturated sodium bicarbonate and brine. The aqueous phase was extracted with ethyl ether and the combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to give the title material (9.6 g, 100% crude) as a yellowish oil which was used for the next reaction.

Workup

customthe organic phase was separated
washwashed with water (2×), saturated sodium bicarbonate and brine
extractionThe aqueous phase was extracted with ethyl ether
dry with materialthe combined organic extracts were dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-7f8db51b684a4a34ad840fbf86d615a2
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713515B2

Linked notes

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