Toluene → HCID 21273108, compound

HRID 2231852Notes

Reaction equation

HRID 2231852 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 hexane as eluant. The desired 1-(2-nonylphenyl)-transhexene is obtained in the form of a pale yellow oil. IR (CH2Cl2): 2960, 2930, 2855, 1465, 970 cm-1.

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-5d4b7775a7684f0fb7f309bcc7fcea6a
Source dataset
uspto-grants-1988_11
Patent number
US04785004

Reaction notes

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