(Trans,trans)-4'-ethyl-[1,1'-bi(cyclohexan)]-4-ol → Trifluoroacetic acid 4-(4-ethylcyclohexyl)cyclohexyl ester

HRID 2119270Notes

Reaction equation

HRID 2119270 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](C1C2N=NNC=2C=CC=1)=[O:4].[CH2:16]([CH:18]1[CH2:23][CH2:22][CH:21]([CH:24]2[CH2:29][CH2:28][CH:27]([OH:30])[CH2:26][CH2:25]2)[CH2:20][CH2:19]1)[CH3:17]>C1COCC1>[CH2:16]([CH:18]1[CH2:23][CH2:22][CH:21]([CH:24]2[CH2:29][CH2:28][CH:27]([O:30][C:3](=[O:4])[C:2]([F:15])([F:14])[F:1])[CH2:26][CH2:25]2)[CH2:20][CH2:19]1)[CH3:17]

Participants

4

Reactant 2

HCID 22242489(Trans,trans)-4'-ethyl-[1,1'-bi(cyclohexan)]-4-olHCID 178519451HCID 178519451, compound

Product 1

HCID 20615180Trifluoroacetic acid 4-(4-ethylcyclohexyl)cyclohexyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trifluoroacetylbenzotriazole in an amount of 4.0 g (18.6 mmol) was dissolved in 50 ml of THF, 2.3 g (10.9 mmol) of 4-(4-ethylcyclohexyl)cyclohexanol was added thereto, they were subjected to a reflux for 1 hour, and then the solvent was distilled off. After the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=8/1), the solvent was distilled off, and the residue was subjected twice to recrystallization by using heptane to give 1.8 g (5.9 mmol) of trifluoroacetic acid 4-(4-ethylcyclohexyl)cyclohexyl ester. Yield of this compound based on 4-(4-ethylcyclohexyl)cyclohexanol was 54%.

Workup

  1. temperaturea reflux for 1 hour
  2. distillationthe solvent was distilled off
  3. customAfter the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=8/1)
  4. distillationthe solvent was distilled off
  5. customthe residue was subjected twice to recrystallization

Sources & evidence

ORD record
ord-f182d41ed2484b03b954b542899217b5
Source dataset
uspto-grants-2004_02
Patent number
US06685995B1

Reaction notes

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