Toluene → HCID 21273108, compound

HRID 1382698Notes

Reaction equation

HRID 1382698 reaction equation
[CH2:1]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16](O)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[CH2:1]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1/[CH:16]=[CH:17]/[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 21273100HCID 21273100, compound

Product 1

HCID 21273108HCID 21273108, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14.4 g of 1-(2-nonylphenyl)-1-hexanol, 2 g of toluene-4-sulphonic acid monohydrate and 250 ml of toluene is heated under reflux for 3 hours using a water separator. After cooling, the reaction mixture is washed twice with 10% strength (w/v) sodium bicarbonate solution and twice with water. The organic phase is dried over sodium sulphate and concentrated by evaporation in vacuo, and the residue is purified by chromatography on silica gel using hexene as eluant. The desired 1-(2-nonylphenyl)-trans-hexene is obtained in the form of a pale yellow oil.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture is washed twice with 10% strength (w/v) sodium bicarbonate solution and twice with water
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. concentrationconcentrated by evaporation in vacuo
  7. customthe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ea9296340d19428bb6beb97fc2cdde22
Source dataset
uspto-grants-1989_02
Patent number
US04808572

Reaction notes

Loading…