Sulfuric Acid → HCID 86610881, compound

HRID 2424264Notes

Reaction equation

HRID 2424264 reaction equation
S(=O)(=O)(O)O.OC[CH:8]1[CH:13]([CH3:14])[CH:12]2[CH2:15][CH:9]1[CH2:10][CH2:11]2.C=[C:17]1[CH:22](C)[CH:21]2C[CH:18]1[CH2:19][CH2:20]2.[CH3:25]C1C2CC(C=1C)CC2>C1C=CC=CC=1>[CH:17]1([C:13]2([CH3:14])[CH2:8][CH:9]3[CH2:15][C:12]2([CH3:25])[CH2:11][CH2:10]3)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 10720SanteneHCID 979953-Methylbicyclo(2.2.1)heptane-2-methanolHCID 123044203-Methyl-2-methylenenorbornane

Product 1

HCID 86610881HCID 86610881, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a 3 L four-necked flask were placed 820 g of benzene and 53 g of concentrated sulfuric acid, to which 428 g of the dehydration product of 2-hydroxymethyl-3-methylbicyclo[2.2.1]heptane containing 2-methylene-3-methylbicyclo[2.2.1]heptane and 2,3-dimethylbicyclo[2.2.1]hept-2-ene as main ingredients was added dropwise over 3 hours to perform alkylation. The reaction mixture was washed with a dilute aqueous NaOH solution and with a saturated aqueous sodium chloride solution. After the removal of unreacted benzene by distillation, the washed mixture was placed in a 2 L autoclave together with 18 g of a nickel/diatomaceous earth hydrogenation catalyst (N-113, manufactured by Nikki Chemical Co., Ltd.) and was hydrogenated (hydrogen pressure: 2 MPa, reaction temperature: 250° C., reaction time: 8 hours). After completion of the reaction, the catalyst was removed by filtration and the filtrate was distilled under reduced pressure to obtain 210 g of the desired cyclohexyl-dimethylbicyclo[2.2.1]heptane (Fluid D). The results of the measurements of the properties and the traction coefficient are shown in Table 1, from which it will be appreciated that the traction coefficient is low.

Workup

  1. customIn a 3 L four-necked flask were placed
  2. additionwas added dropwise over 3 hours
  3. washThe reaction mixture was washed with a dilute aqueous NaOH solution and with a saturated aqueous sodium chloride solution
  4. customAfter the removal of unreacted benzene
  5. distillationby distillation
  6. custom(hydrogen pressure: 2 MPa, reaction temperature: 250° C., reaction time: 8 hours)
  7. customAfter completion of the reaction
  8. customthe catalyst was removed by filtration
  9. distillationthe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-b0c91c65cdb24004bd5cb2536d5b3953
Source dataset
uspto-grants-2011_06
Patent number
US07964540B2

Reaction notes

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