Sodium Hydroxide → 4-(4-Bromophenyl)cyclohexane carboxylic acid methyl ester

HRID 1893068Notes

Reaction equation

HRID 1893068 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[N+]([O-])([O-])=O.[Tl+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[Br:30]Br.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:6][CH2:7][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([Br:30])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1)=[O:4]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 159690Thallic nitrateHCID 754723Methyl 4-phenylcyclohexane-1-carboxylate

Product 1

HCID 584532034-(4-Bromophenyl)cyclohexane carboxylic acid methyl esterYield 70.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

10 g (45.8 mmol) of methyl-4-phenylcyclohexane carboxylate and 3.46 g (7.78 mmol) of thallium(III) nitrate were dissolved in chloroform. 120 mL of the resulting solution was cooled to 0° C. 1.87 mL (36.6 mmol) of Br2 was added dropwise to the resulting solution, and reacted at room temperature for 24 hours. Then, the reacted solution was neutralized by 10% NaOH aqueous solution, extracted by chloroform, dried by anhydrous Na2SO4, and filtered. The filtrate was concentrated under reduced pressure. The resulting material was recrystallized from ethanol to obtain 7.7 g (57%) 4-(4-bromophenyl)cyclohexane carboxylic acid methyl ester.

Workup

  1. customreacted at room temperature for 24 hours
  2. extractionextracted by chloroform
  3. dry with materialdried by anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe resulting material was recrystallized from ethanol

Sources & evidence

ORD record
ord-86ff1724b252491ea9bf0b41905cf4a2
Source dataset
uspto-grants-2013_08
Patent number
US08512598B2

Reaction notes

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