Diethyl Ether → 2,4-Dichloro-beta-(1-methylethyl)benzeneethanol

HRID 745275Notes

Reaction equation

HRID 745275 reaction equation
O(CC)CC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[CH:20]([CH:25]([CH3:27])[CH3:26])[C:21](OC)=[O:22].[OH-].[Na+]>O>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[CH:20]([CH:25]([CH3:27])[CH3:26])[CH2:21][OH:22]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23315370Methyl 2,4-dichloro-alpha-(1-methylethyl)benzeneacetate

Product 1

HCID 233154532,4-Dichloro-beta-(1-methylethyl)benzeneethanolYield 93.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 140 parts of 1,1'-oxybisethane are added 3 parts of lithium aluminium hydride. Then there is added dropwise a solution of 24.5 parts of methyl 2,4-dichloro-α-(1-methylethyl)benzeneacetate in 35 parts of 1,1'-oxybisethane while cooling in a water-bath. Upon completion, stirring is continued overnight at room temperature. There are added dropwise successively 3 parts of a sodium hydroxide solution 50% and 1 part of water, and the whole is stirred for one hour at room temperature. The mixture is filtered over hyflo and the filter-cake is washed with 2,2'-oxybispropane. The filtrate is evaporated, yielding 20.5 parts (93.5%) of 2,4-dichloro-β-(1-methylethyl)benzeneethanol as a residue.

Workup

  1. temperaturewhile cooling in a water-bath
  2. stirringthe whole is stirred for one hour at room temperature
  3. filtrationThe mixture is filtered over hyflo
  4. washthe filter-cake is washed with 2,2'-oxybispropane
  5. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-513e084e3b65458cb6808225d959f842
Source dataset
uspto-grants-1986_07
Patent number
US04598085

Reaction notes

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