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

HRID 1589588Notes

Reaction equation

HRID 1589588 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[C:3]1=[O:9].[CH3:11][Mg]Br.[Cl-].[NH4+]>CCOCC>[CH3:11][C:3]1([OH:9])[C:4]([CH3:8])([CH3:7])[CH2:5][CH2:6][C:2]1([CH3:10])[CH3:1]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1382872,2,5,5,-TetramethylcyclopentanoneHCID 178418573HCID 178418573, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2,2,5,5-tetramethylcyclopentanone (30 g, 0.215 mole) in ether (50 ml) was treated, under nitrogen, with a 3M solution of methyl magnesium bromide in ether (100 ml). The reaction mixture was stirred overnight at room temperature and saturated aqueous ammonium chloride (65 ml) then added dropwise. The mixture was stirred for 10 minutes, the ether solution decanted and the solid residue triturated with ether. The ether extracts were dried (Na2SO4) and evaporated under reduced pressure to give crude 1,2,2,5,5-pentamethylcyclopentanol (30 g) which was used without further purification.

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. customthe ether solution decanted
  3. customthe solid residue triturated with ether
  4. dry with materialThe ether extracts were dried (Na2SO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2ef27ddb5eb64f2ead7159995d20197c
Source dataset
uspto-grants-1986_02
Patent number
US04571345

Reaction notes

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