Isopropanol → [[1,1'-Bi(cyclohexane)]-1-yl]methanol

HRID 1746338Notes

Reaction equation

HRID 1746338 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:2](C=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.[H][H].C[CH:18]([OH:20])C>>[C:9]1([CH2:18][OH:20])([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 121052(1,1'-Biphenyl)-2-carboxaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 21527964[[1,1'-Bi(cyclohexane)]-1-yl]methanolYield 80%

Conditions

Temperature
150 °C

Procedure

To a 5000 ml autoclave, 910 g of 2-propanol (IPA, Wako Pure Chemical Industries, special grade), 364 g of biphenyl aldehyde made by Mitsubishi Gas Chemical (2.0 mol), 7.3 g of 5% Ru/Al2O3 (made by N. E. CHEMCAT) and 10 MPa of hydrogen were charged, and stirred at 150° C. for 8 h. After cooling, a catalyst was filtered under an inert gas atmosphere. After a solvent was removed, distillation was conducted under reduced pressure to obtain bicyclohexyl methanol (BCHM) (80% yield, 99% purity).

Workup

  1. additionwere charged
  2. temperatureAfter cooling
  3. filtrationa catalyst was filtered under an inert gas atmosphere
  4. customAfter a solvent was removed
  5. distillationdistillation

Sources & evidence

ORD record
ord-daed2e528e384ca9a966ab710947e4fd
Source dataset
uspto-grants-2015_10
Patent number
US09150491B2

Reaction notes

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