tert-Butanol → 1-(2-Ethyl-butyl)-cyclohexanecarboxylic acid

HRID 873511Notes

Reaction equation

HRID 873511 reaction equation
[CH2:1]([CH:3]([CH2:13][CH3:14])[CH2:4][C:5]1([C:11]#N)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:2].[OH-:15].[Na+].C([OH:21])(C)(C)C>>[CH2:1]([CH:3]([CH2:13][CH3:14])[CH2:4][C:5]1([C:11]([OH:21])=[O:15])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:2]

Participants

4

Reactant 3

HCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 442426841-(2-Ethylbutyl)cyclohexanecarbonitrile

Product 1

HCID 104887511-(2-Ethyl-butyl)-cyclohexanecarboxylic acid

Conditions

Temperature
280 °C

Procedure

A stream of 1-(2-ethyl-butyl)-cyclohexanecarbonitrile (0.5 g, 2.59 mmol) in tert-butanol (12.5 mL, 0.2 M, flow=0.18 mL/min; Knauer WellChrom HPLC K-501 pump) was combined with a second stream containing aqueous sodium hydroxide solution (2.0 M, 50 mL, flow=0.70 mL/min; Knauer WellChrom HPLC K-501 pump) using a custom made static micromixer (internal volume ca. 0.1 mL). The resulting mixture was directed through a stainless steel coil reactor (volume=53 mL, ID=2.1 mm; Supelco 304 stainless steel; nominal residence time of 1 h, which doesn't take the volume expansion of the solvent mixture into account) equipped with a total back pressure valve of 2500 psi and heated to 280° C. by means of a HP 6890 Series GC Oven System.

Workup

  1. customThe resulting mixture was directed through a stainless steel coil reactor
  2. customnominal residence time of 1 h, which
  3. customequipped with a total back pressure valve of 2500 psi

Sources & evidence

ORD record
ord-2593ae264e8e4840bdc98da0436f9cb6
Source dataset
uspto-grants-2015_03
Patent number
US08975438B2

Reaction notes

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