Ammonium Chloride → 1,2,2,5,5-Pentamethylcyclopentanol

HRID 986864Notes

Reaction equation

HRID 986864 reaction equation
C[Mg]Br.[CH3:4]COCC.[CH3:9][C:10]1([CH3:18])[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[C:11]1=[O:17].[Cl-].[NH4+]>CCOCC>[CH3:4][C:11]1([OH:17])[C:12]([CH3:16])([CH3:15])[CH2:13][CH2:14][C:10]1([CH3:18])[CH3:9]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1382872,2,5,5,-TetramethylcyclopentanoneHCID 178467822HCID 178467822, compound

Product 1

HCID 200340841,2,2,5,5-Pentamethylcyclopentanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

100 ml of a 3M methylmagnesium bromide/ether solution was added to a solution of 30 g of 2,2,5,5-tetramethylcyclopentanone in 50 ml of ether under a nitrogen gas atmosphere, and the mixture was stirred at room temperature overnight. Then, 65 ml of aqueous saturated ammonium chloride solution was added dropwise thereto and the mixture was stirred for 10 minutes. The ether layer was subjected to decantation and the residue was extracted with ether. The ether layers were dried over anhydrous sodium sulfate, and concentrated under reduced pressure, whereby 30 g of 1,2,2,5,5-pentamethylcyclopentanol was obtained.

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. extractionthe residue was extracted with ether
  3. dry with materialThe ether layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f85c748fc2e042198ac209240dc62694
Source dataset
uspto-grants-1987_12
Patent number
US04716241

Reaction notes

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