4-(4-(4-Hydroxycyclohexyl)cyclohexyl)-1-propylbenzene → Trifluoroacetic acid 4-(4-(4-propylphenyl)cyclohexyl)cyclohexyl ester

HRID 2119273Notes

Reaction equation

HRID 2119273 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](C1C2N=NNC=2C=CC=1)=[O:4].[OH:16][CH:17]1[CH2:22][CH2:21][CH:20]([CH:23]2[CH2:28][CH2:27][CH:26]([C:29]3[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][CH3:37])=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)[CH2:19][CH2:18]1>C1COCC1>[CH2:35]([C:32]1[CH:33]=[CH:34][C:29]([CH:26]2[CH2:25][CH2:24][CH:23]([CH:20]3[CH2:19][CH2:18][CH:17]([O:16][C:3](=[O:4])[C:2]([F:15])([F:14])[F:1])[CH2:22][CH2:21]3)[CH2:28][CH2:27]2)=[CH:30][CH:31]=1)[CH2:36][CH3:37]

Participants

4

Reactant 2

HCID 234403894-(4-(4-Hydroxycyclohexyl)cyclohexyl)-1-propylbenzeneHCID 178519451HCID 178519451, compound

Product 1

HCID 20615149Trifluoroacetic acid 4-(4-(4-propylphenyl)cyclohexyl)cyclohexyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trifluoroacetylbenzotriazole described above in an amount of 4.0 g (18.6 mmol) was dissolved in 50 ml of THF, 2.5 g (8.3 mmol) of 4-(4-(4-hydroxycyclohexyl)cyclohexyl)-1-propylbenzene was added thereto, they were refluxed 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=3/1), the solvent was distilled off. The residue was subjected twice to recrystallization by using mixed solvent of heptane/ethyl acetate (1/5) to give 1.2 g (3.0 mmol) of trifluoroacetic acid 4-(4-(4-propylphenyl)cyclohexyl)cyclohexyl ester. Yield of this compound was 36%.

Workup

  1. temperaturethey were refluxed 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=3/1)
  4. distillationthe solvent was distilled off
  5. customThe residue was subjected twice to recrystallization
  6. additionby using mixed solvent of heptane/ethyl acetate (1/5)

Sources & evidence

ORD record
ord-eb0ecd253a614c979dde57494f7caaf2
Source dataset
uspto-grants-2004_02
Patent number
US06685995B1

Reaction notes

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