p-Toluenesulfonic acid monohydrate → 1,2-Dihydro-4,6,8-Trimethylnaphthalene

HRID 487120Notes

Reaction equation

HRID 487120 reaction equation
O[C:2]1([CH3:14])[C:11]2[C:6](=[C:7]([CH3:13])[CH:8]=[C:9]([CH3:12])[CH:10]=2)[CH2:5][CH2:4][CH2:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:14][C:2]1[C:11]2[C:6](=[C:7]([CH3:13])[CH:8]=[C:9]([CH3:12])[CH:10]=2)[CH2:5][CH2:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 157517571-Hydroxy-1,5,7-trimethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 5939371,2-Dihydro-4,6,8-TrimethylnaphthaleneYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Following the procedure of Example 1, step 2, 26.64 g (0.140 mol) of 1-hydroxy-1,5,7-trimethyl-1,2,3,4-tetrahydronaphthalene in 300 ml of toluene was reacted with 0.30 g of p-toluenesulphonic acid monohydrate. Vacuum distillation yielded 20.49 g (85%) of the title product as a pale yellow liquid, b.p. 67°-70° C./0.12 mm of Hg. NMR δ(CDCl3) 2.04 (3H, m), 2.21-2.25 (2H, m), 2.25 (3H, s), 2.30 (3H, s), 2.66 (2H, t, J=8.1 Hz), 5.83 (1H, m), 6.87 (1H, s), 6.94 (1H, s).

Workup

  1. distillationVacuum distillation

Sources & evidence

ORD record
ord-712c1b14ba444374bfcbbcfc42f67913
Source dataset
uspto-grants-1994_03
Patent number
US05294618

Reaction notes

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