tert-Butanol → cyclohexanecarboxylic acid tert-butyl ester

HRID 2294779Notes

Reaction equation

HRID 2294779 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]1[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]1.[C:25](O)([CH3:28])([CH3:27])[CH3:26].CN(C)C1C=CN=CN=1>C(Cl)Cl>[CH2:16]1[CH2:21][CH2:20][CH:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 7413Cyclohexanecarboxylic acidHCID 10868DicyclohexylcarbodiimideHCID 5791964-(Dimethylamino)pyrimidine

Product 1

HCID 11816271cyclohexanecarboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 48.2 g of dicyclohexylcarbodiimide in 100 ml of methylene chloride is added dropwise at room temperature with stirring to a solution of 27.7 g (0.2 mol) of 4-cyclohexanecarboxylic acid, 28.9 g of tert-butanol and 24 g of 4-dimethylaminopyrimidine in 200 ml of methylene chloride. The mixture is stirred for 24 hours at room temperature, dicyclohexylurea is removed by filtration, and the product is extracted twice by stirring with water. The organic phase is dried and concentrated. The crude product is purified by distillation on a thin-film evaporator (150°/0.4 mm). This gives 20 g (51.8% of theory) of a colorless oil.

Workup

  1. customdicyclohexylurea is removed by filtration
  2. extractionthe product is extracted twice
  3. stirringby stirring with water
  4. customThe organic phase is dried
  5. concentrationconcentrated
  6. distillationThe crude product is purified by distillation on a thin-film evaporator (150°/0.4 mm)

Sources & evidence

ORD record
ord-116e0d675d954843a3bac749f0263ced
Source dataset
uspto-grants-1997_11
Patent number
US05691321

Reaction notes

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