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

HRID 486413

Reaction equation

HRID 486413 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([CH:12]([CH3:14])[CH3:13])[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1.[CH2:15]=[CH:16][C:17](C)([CH3:19])[CH3:18].[CH2:21]1CCCCC1>>[CH3:13][C:12]1([CH3:21])[C:5]2[C:10](=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=2)[C:17]([CH3:19])([CH3:18])[CH:16]([CH3:15])[CH2:14]1

Participants

5

Reactant 4

HCID 7463P-CymeneHCID 8078CyclohexaneHCID 112103,3-Dimethyl-1-buteneHCID 6451240Aluminum(III) Chloride

Product 1

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

Conditions

Temperature
16 °C

Procedure

The starting material 1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (HMT) was prepared by substantially following the procedures of Frank, U.S. Pat. No. 4,877,913. Specifically, a 100 ml, four-necked, round bottom flask was charged with cyclohexane (7.17 g) and anhydrous aluminum chloride (1.004 g), and cooled to about 16° C. A 60 ml addition funnel was charged with para-cymene (39.87 g), diisobutylene-2 (8.34 g), and neohexene (6.25 g) and connected to the flask. The funnel mixture was added to the flask over a period of about one hour and the flask mixture stirred 30 minutes following addition, while maintaining the temperature at about 16° C. The reaction was then quenched with deionized water (15 ml), and the organic phase separated and washed with, in order, 5% HCl, 10% Na2CO3, and 50% brine. The aqueous layers were then dried over K2CO3, filtered, and evaporated to yield a crude product (41.13 g) containing 28.16 weight % HMT.

Workup

  1. additionA 60 ml addition funnel
  2. additionThe funnel mixture was added to the flask over a period of about one hour
  3. additionaddition
  4. temperaturewhile maintaining the temperature at about 16° C
  5. customThe reaction was then quenched with deionized water (15 ml)
  6. customthe organic phase separated
  7. washwashed with, in order, 5% HCl, 10% Na2CO3, and 50% brine
  8. dry with materialThe aqueous layers were then dried over K2CO3
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-72da079ef4fd4c10be586bd406d00419
Source dataset
uspto-grants-1994_03
Patent number
US05292719

Linked notes

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