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

HRID 2291403Notes

Reaction equation

HRID 2291403 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-a97ca8e60c404a7b93f7ece5f59b3857
Source dataset
uspto-grants-1989_01
Patent number
US04795831

Reaction notes

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