p-Toluenesulfonic acid → 1-(4-Methoxyphenyl)-2-[4-(4-pentylcyclohexen-1-yl)-phenyl]-acetylene

HRID 974158Notes

Reaction equation

HRID 974158 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3(O)[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.BrC1C=CC(C#CC2C=CC(OC)=CC=2)=CC=1.C(C1CCC(=O)CC1)CCCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]#[C:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:19][CH:18]=3)=[CH:15][CH:16]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 5660974-PentylcyclohexanoneHCID 117090154-[(4-bromophenyl) ethynyl] phenyl methyl etherHCID 679441214-Methoxy-4'-(1-hydroxy-4-pentylcyclohexyl)-tolan

Product 1

HCID 199838311-(4-Methoxyphenyl)-2-[4-(4-pentylcyclohexen-1-yl)-phenyl]-acetylene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

0.2 mol of 4-methoxy-4'-(1-hydroxy-4-pentylcyclohexyl)-tolan (prepared by reaction of a Grignard compound of 4-bromo-4'-methoxytolan with 4-pentylcyclohexanone) is heated in 400 ml of toluene and with 1 g of p-toluenesulfonic acid for 1 hour using a water separator. The reaction mixture is washed, dried and evaporated. Customary working up gives 1-(4-methoxyphenyl)-2-[4-(4-pentylcyclohexen-1-yl)-phenyl]-acetylene.

Workup

  1. washThe reaction mixture is washed
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-e18e44fb9030425ab55c9db7b212f32e
Source dataset
uspto-grants-1991_11
Patent number
US05068053

Reaction notes

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