Propylene Oxide → 3-tert-Butylcyclohexanol

HRID 1613546Notes

Reaction equation

HRID 1613546 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([OH:11])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:12]1[O:16][CH:13]1[CH2:14][CH3:15].C(C1CCCCC1O)(C)(C)C.C1OC1C>>[C:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([OH:11])[CH2:6]1)([CH3:4])([CH3:2])[CH3:3].[C:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([O:11][CH2:12][CH:13]([OH:16])[CH2:14][CH3:15])[CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6378Propylene OxideHCID 78341,2-EpoxybutaneHCID 260682-tert-ButylcyclohexanolHCID 126029233-tert-Butylcyclohexanol

Product 2

HCID 126029233-tert-ButylcyclohexanolHCID 197740641-(3-Tert-butylcyclohexyloxy)-2-butanol

Procedure

The synthesis was carried out in the same manner as described in Example 1, except that 30.0 g (0.192 mol) of 3-tert-butylcyclohexanol (cis:trans=2:8) and 13.8 g (0.192 mol) of 1,2-butyleneoxide were used instead of 30.0 g (0.192 mol) of 2-tert-butylcyclohexanol (cis:trans=8:2) and 11.1 g (0.192 mol) of propyleneoxide. 11.3 g of 3-tert-butylcyclohexanol and 9.3 g of 1-(3-tert-butylcyclohexyloxy)-2-butanol (cis:trans=2:8) (bp. 145° to 148° C./10 mm Hg) were obtained in a 32% yield. Then, the cis-trans isomers of 1-(3-tert-butylcyclohexyloxy)-2-butanol were separated from each other in the same manner as described in Example 1.

Sources & evidence

ORD record
ord-1d7e7a392952438f843f9d8a92052efa
Source dataset
uspto-grants-1993_03
Patent number
US05194423

Reaction notes

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