Sulfuric Acid → Benzene, 1-methyl-4-[1-(chloromethyl)-1-methylethyl]

HRID 486399Notes

Reaction equation

C(C1[C:12]2[C:7](=[CH:8][C:9](C)=[CH:10][CH:11]=2)[C:6](C)(C)C1C)(C)C.[CH2:17]([Cl:21])[C:18](=[CH2:20])[CH3:19].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH3:20][C:18]([C:10]1[CH:11]=[CH:12][C:7]([CH3:6])=[CH:8][CH:9]=1)([CH3:19])[CH2:17][Cl:21]

Participants

Conditions

Temperature: 40 °C

Procedure

To prepare the 1-isopropyl-2,3,3,5-tetramethylindane, the procedures of Traas et al., U.S. Pat. No. 4,352,748 are substantially followed. Specifically, methallyl chloride (24 g) is added to a mixture of toluene (92 g) and concentrated sulfuric acid (49 g), while maintaining the temperature at about 40° C. The reaction mixture is stirred for half an hour, after which time the layers are separated. The organic layer is washed neutral with soda solution, dried on magnesium sulfate and evaporated. The residue is distilled under diminished pressure to obtain 2-methyl-2 (para-tolyl)propyl chloride. A mixture of 2 methyl-2-(para-tolyl)propyl chloride (18 g) and tert-amyl chloride (10 g) is added to aluminum chloride (10 g) dissolved in nitromethane (50 ml), at a temperature of between about 5° C. and 10 ° C. The reaction mixture is allowed to warm to room temperature, with stirring, over a period of about one hour. The reaction mixture is then poured over ice, and extracted three times with ether. The solution in ether is washed to neutrality, dried on magnesium sulfate and evaporated. The residue is distilled under diminished pressure to yield 1-isopropyl-2,3,3,5-tetramethylindane.

Workup

customafter which time the layers are separated
washThe organic layer is washed neutral with soda solution
customdried on magnesium sulfate
customevaporated
distillationThe residue is distilled under diminished pressure

Sources & evidence

ORD record: ord-afc9d1719e214af7926fdb841e968713
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05292720

Reaction notes

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