Toluene → 1,1,6-Trimethyl-4-(propan-2-yl)-1,2,3,4-tetrahydronaphthalene

HRID 979756Notes

Reaction equation

HRID 979756 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5]C=[CH:3][CH:2]=1.[CH3:8][C:9](O)([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH3:10].[CH3:18]CCCCC>>[CH:14]([CH:13]1[C:5]2[C:8](=[CH:3][CH:2]=[C:1]([CH3:7])[CH:6]=2)[C:9]([CH3:10])([CH3:18])[CH2:11][CH2:12]1)([CH3:16])[CH3:15]

Participants

4

Reactant 3

HCID 1140TolueneHCID 8058HexaneHCID 801835-Hepten-2-ol, 2,6-dimethyl-

Product 1

HCID 2264181,1,6-Trimethyl-4-(propan-2-yl)-1,2,3,4-tetrahydronaphthalene

Conditions

Temperature
10 °C

Procedure

1050 g of sulphuric acid are provided and a mixture of 1.5 l of toluene and 497 g of 2,6-dimethyl-hept-5-en-2-ol are added dropwise during 35 minutes while cooling (10° C.). The mixture is stirred at room temperature for 1.5 hours. The mixture is now diluted with hexane, poured on to ice, washed neutral, dried and evaporated. After distillation there are obtained 455 g of 1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydro-naphthalene (purity 75%).

Workup

  1. additionare added dropwise during 35 minutes
  2. additionpoured on to ice
  3. washwashed neutral
  4. customdried
  5. customevaporated
  6. distillationAfter distillation

Sources & evidence

ORD record
ord-87fa37a644f14e95a7e4c093549cc9ad
Source dataset
uspto-grants-1987_01
Patent number
US04634548

Reaction notes

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