Hydrochloric Acid → 4-(1-Phenylcyclohexyl)butanoic acid

HRID 71249Notes

Reaction equation

HRID 71249 reaction equation
[C:1]1([C:7]2([CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO>[C:1]1([C:7]2([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 66685524Ethyl 4-(1-phenylcyclohexyl)butanoate

Product 1

HCID 666852144-(1-Phenylcyclohexyl)butanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-(1-phenylcyclohexyl)butanoate (0.211 g, 0.77 mmol) in MeOH (5 mL) was added 1M sodium hydroxide (1.155 mL, 1.155 mmol) and the mixture was stirred at room temp for 5 hrs. Then additional 0.39 ml of 1M NaOH was added and stirring was continued for 3 hrs. To the mixture was added 2 ml of 1N HCl and extracted with EtOAc (2×). The combined extracts were washed with brine, dried over Na2SO4 and evaporated to give an oily residue, which became white solid upon storing at room temp.

Workup

  1. stirringstirring
  2. waitwas continued for 3 hrs
  3. extractionextracted with EtOAc (2×)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customto give an oily residue, which
  8. customupon storing at room temp.

Sources & evidence

ORD record
ord-2382ce3ee0144836ac8d6acee27bca45
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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