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

HRID 1168156Notes

Reaction equation

HRID 1168156 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

4

Reactant 2

HCID 1118Sulfuric AcidHCID 134632862-Methyl-5-(p-tolyl)-pentan-2-ol

Product 1

HCID 2263961,1,7-Trimethyl-1,2,3,4-tetrahydronaphthaleneYield 101.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

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 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

  1. customthe organic phase was separated
  2. washwashed with water (2×), saturated sodium bicarbonate and brine
  3. extractionThe aqueous phase was extracted with ethyl ether
  4. dry with materialwere dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bec49009130144ecaa6898b043c56b28
Source dataset
uspto-grants-2003_09
Patent number
US06624154B1

Reaction notes

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