1,2-Butanediol → 2-tert-Butylcyclohexyloxybutanol

HRID 1757685

Reaction equation

HRID 1757685 reaction equation
[C:1]([CH:5]1[CH2:16][CH2:15][CH2:14][CH2:13][C:6]21[O:10][CH:9]([CH2:11][CH3:12])[CH2:8][O:7]2)([CH3:4])([CH3:3])[CH3:2].C(C1CCCCC1=O)(C)(C)C.C(O)C(O)CC>[Pd].[Ru]>[C:1]([CH:5]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:6]1[O:7][CH2:8][CH:9]([OH:10])[CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 114291,2-ButanediolHCID 1026812-tert-ButylcyclohexanoneHCID 157895866-t-Butyl-2-ethyl-1,4-dioxaspiro[4.5]decane

Product 1

HCID 1644222-tert-ButylcyclohexyloxybutanolYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 23950RutheniumCatalyst

Procedure

A 500 ml capacity autoclave was charged with 150 g (0.68 mol) of 6-t-butyl-2-ethyl-1,4-dioxaspiro[4.5]decane which has been prepared from 2-t-butylcyclohexanone and 1,2-butanediol, 1.47 g of a catalyst of 5% palladium supported on active carbon and 0.03 g of a catalyst of 5% ruthenium supported on active carbon. The reaction was carried out under ahydrogen pressure of 70 kg/cm2 and at a temperature of 190° C. for 10 hours until completion of the absorption of hydrogen. In this way, 134.7 g of 1-(2-t-butylcyclohexyloxy)-2-butanol was obtained (yield=89%; cis:trans=66:34).

Workup

  1. customThe reaction was carried out under ahydrogen pressure of 70 kg/cm2 and at a temperature of 190° C. for 10 hours until completion of the absorption of hydrogen

Sources & evidence

ORD record
ord-c878a16902cb46fdaf879a35f20da910
Source dataset
uspto-grants-1995_08
Patent number
US05446208

Linked notes

Loading…