Hydrochloric Acid → 2-tert-Butylcyclohexanol

HRID 1613541Notes

Reaction equation

HRID 1613541 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[OH:11])([CH3:4])([CH3:3])[CH3:2].[H][H].[CH2:14]1[O:17][CH:15]1[CH3:16].Cl>O1CCCC1>[C:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[OH:11])([CH3:4])([CH3:2])[CH3:3].[C:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[O:11][CH2:14][CH:15]([OH:17])[CH3:16])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6378Propylene OxideHCID 260682-tert-ButylcyclohexanolHCID 178418361HCID 178418361, compound

Product 2

HCID 260682-tert-ButylcyclohexanolHCID 193892761-(2-t-Butylcyclohexyloxy)-2-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a 300 ml round bottom flask provided with a Dimroth condenser and a dropping funnel, 7.5 g (0.194 mol) of sodium hydride (62 weight % mineral oil dispersion type) and 30 ml of tetrahydrofuran were added and heated at 60° C. under a nitrogen gas flow. Then, to this solution a mixture of 30.0 g (0.192 mol) of 2-tert-butylcyclohexanol (cis:trans=8:2) and 30 ml of tetrahydrofuran was added dropwise in approximately 30 minutes, and the mixed solution was stirred under reflux for 24 hours until the generation of hydrogen gas had stopped. The reacted mixed solution was cooled to 40° C., and after dropwise adding 11.1 g (0.192 mol) of propyleneoxide to the mixed solution, the solution was further stirred under reflux for 48 hours. The mixed solution was neutralized by 3N hydrochloric acid, and the organic layer was separated from the water layer. Distillation was then conducted and 9.9 g of 2-tert-butylcyclohexanol and 24.2 g of 1-(2-tert-butylcyclohexyloxy)-2-propanol (cis:trans=8:2) (bp. 112° to 113° C./5 mm Hg) were obtained in a 59% yield. Further, the cis-trans isomers of 1-(2-tert-butylcyclohexyloxy)-2-propanol were separated from each other by column chromatography using a developing solvent composed of Kieselgel 60 (trademark) of Merck Corporation and hexane:ethyl acetate =95:5.

Workup

  1. additionwere added
  2. additionwas added dropwise in approximately 30 minutes
  3. additionThe reacted mixed solution
  4. temperaturewas cooled to 40° C.
  5. stirringthe solution was further stirred
  6. temperatureunder reflux for 48 hours
  7. customthe organic layer was separated from the water layer
  8. distillationDistillation

Sources & evidence

ORD record
ord-da261da00444442e852185bd8a0c41fb
Source dataset
uspto-grants-1993_03
Patent number
US05194423

Reaction notes

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