Hydrochloric Acid → 3-((4-Propylcyclohexyl)cyclohexyl)phenyl propanoate

HRID 17751Notes

Reaction equation

HRID 17751 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[CH2:6]([CH:9]1[CH2:14][CH2:13][CH:12]([C:15]2([C:21]3[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=3)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:11][CH2:10]1)[CH2:7][CH3:8].O.Cl>N1C=CC=CC=1>[C:1]([O:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:15]2([CH:12]3[CH2:13][CH2:14][CH:9]([CH2:6][CH2:7][CH3:8])[CH2:10][CH2:11]3)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:22]=1)(=[O:4])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 62324Propionyl chlorideHCID 684282843-((4-Propylcyclohexyl)cyclohexyl)phenol

Product 1

HCID 684297793-((4-Propylcyclohexyl)cyclohexyl)phenyl propanoateYield 109.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under a nitrogen atmosphere, 1.7 g of propanoyl chloride was added to 5.0 g of 3-((4-propylcyclohexyl)cyclohexyl)phenol (3) dissolved in 10 mL of pyridine under cooling with iced water, and after completing dropwise addition, the mixture was stirred at ambient temperature for 2 hours. The resulting solution was added to 20 mL of 3N hydrochloric acid. The aqueous layer was extracted with diethyl ether, which was added to the organic layer, and the organic layer was washed with a saturated salt solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 6.52 g of 3-((4-propylcyclohexyl)cyclohexyl)phenyl propanoate (4).

Workup

  1. additionaddition
  2. extractionThe aqueous layer was extracted with diethyl ether, which
  3. additionwas added to the organic layer
  4. washthe organic layer was washed with a saturated salt solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-40c8bef0bc5d470f8c1c4b99c8dc2dc8
Source dataset
uspto-grants-2010_06
Patent number
US07740769B2

Reaction notes

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