Sulfuric Acid → HCID 20541017, compound

HRID 1065589Notes

Reaction equation

HRID 1065589 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.S(=O)(=O)(O)O>C(OCC)C>[C:11]1([CH:10]([OH:17])[CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 7412Benzoyl chlorideHCID 178418336HCID 178418336, compound

Product 1

HCID 20541017HCID 20541017, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Four liters of an ethyl ether solution containing 500 g of benzyl magnesium chloride were added slowly to a mixture of 1.5 Kg benzoyl chloride and 1 l of ethyl ether while cooling the whole mass. Thereafter, the whole mass was incorporated with 1 l of 30% sulphuric acid, agitated, incorporated with an alkali for neutralizing the sulphuric acid, washed with water and then distilled to remove therefrom 183 g of a distillate (phenyl-o-tolylketone) boiling in the range of 164°-169° C. at 9 mm Hg and then obtain 200 g of a distillate (1,2,3-triphenylpropanol) boiling in the range of 224°-235° C. at 8 mm Hg. This propanol (180 g) was incorporated with 150 cc of toluene and 35 g of potassium sulphite to form a mixture which was heated under reflux and, after distillation-off of the toluene, obtain 153 g of 1,2,3-triphenylpropene-1 as the distillate boiling in the range of 185°-188° C. at 0.03 mm Hg. The thus obtained distillate (128 g) was incorporated with 14 g of a rhodium-activated carbon catalyst (rhodium content: 5 wt.%) and 500 cc of n-hexane in a 2-liter autoclave where the resulting mixture was heated to 65° C. for 20 minutes and then at 95° C. for one hour under a hydrogen pressure of 100 Kg/cm2, and further heated to 200° C. for 5 hours under a hydrogen pressure of 200 Kg/cm2 to distil off the n-hexane and then obtain 124 g of a distillate boiling in the range of 140°-146° C. at 0.025 mm Hg and having a refractive index (nD25) of 1.4959. It was found from the NMR spectrum of this distillate that at least 95% of hydrogenation of the aromatic nuclei and aliphatic unsaturated bonds in the distillate had been effected. The distillate was 1,2,3-tricyclohexylpropane having a kinetic viscosity of 7.69 cSt (98.9° C.) and a traction coefficient of 0.075. The distillate or conventional traction fluid obtained herein had a comparatively high viscosity but it was very unsatisfactory in traction coefficient as compared with the traction fluids (II) of this invention (traction coefficient: 0.092~0.094 as indicated in Examples 3-5). Further, it is very uneconomical that the synthesis of such a conventional traction fluid will require a Grignard's reaction using benzyl magnesium chloride and benzoyl chloride.

Workup

  1. temperaturewhile cooling the whole mass
  2. washwashed with water
  3. distillationdistilled
  4. customto remove
  5. customboiling in the range of 164°-169° C. at 9 mm Hg

Sources & evidence

ORD record
ord-c5c44ca80f09492881ee4bc471be937e
Source dataset
uspto-grants-1982_05
Patent number
US04329529

Reaction notes

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