P-Cymene → 1,1,3,4,4,6-Hexamethyltetralin

HRID 462614

Reaction equation

HRID 462614 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:6][CH:7]=1.[C:11](Cl)(C)(C)C.[CH2:16]=[CH:17][C:18](C)([CH3:20])[CH3:19].[Cl-].[Al+3].[Cl-].[Cl-].C([Al](CC)CC)C>>[CH3:9][C:8]1([CH3:11])[C:5]2[C:6](=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[C:18]([CH3:20])([CH3:19])[CH:17]([CH3:16])[CH2:10]1

Participants

6

Reactant 5

HCID 7463P-CymeneHCID 10486tert-BUTYL CHLORIDEHCID 112103,3-Dimethyl-1-buteneHCID 6451240Aluminum(III) ChlorideHCID 16682930Triethylaluminum

Product 1

HCID 1027501,1,3,4,4,6-Hexamethyltetralin

Procedure

p-cymene is reacted with t-butylchloride, neohexene and a mixture of aluminium chloride and triethylaluminium to form 1,1,3,4,4,6-hexamethyl tetralin by the general process described in U.S. Pat. No. 3,856,875 or Japanese 79125647 but modified by cooling the reaction mixture by including dichloromethane in it and refluxing this from the mixture at about 20 mm Hg, thereby maintaining a reaction temperature of about -15° C.

Sources & evidence

ORD record
ord-c6844f2dc1264fd08e3255cb37d2bb8f
Source dataset
uspto-grants-1985_05
Patent number
US04515990

Linked notes

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