2-(4-Chlorophenyl)-2-methylpropionic acid → 2-(4-Chlorophenyl)-2-methylpropanol

HRID 54269Notes

Reaction equation

HRID 54269 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)([CH3:12])[C:9](O)=[O:10]>C(OCC)C>[CH3:12][C:8]([C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=1)([CH3:7])[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 804062-(4-Chlorophenyl)-2-methylpropionic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 130345572-(4-Chlorophenyl)-2-methylpropanolYield 99.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A stirring mixture of 5.4 grams (0.136 mole) of lithium aluminum hydride in 300 mL of diethyl ether is cooled in an ice-water bath, and a solution of 45.0 grams (0.226 mole) of 2-methyl-2-(4-chlorophenyl)propanoic acid in 300 mL of diethyl ether is added dropwise during a one hour period. Upon completion of addition, the reaction mixture is allowed to warm to ambient temperature where it is stirred for about 18 hours. After this time the reaction mixture is cooled in an ice-water bath, and the reaction is quenched with the careful dropwise addition of water. Upon completion of addition, the reaction mixture is made basic with the slow addition of aqueous 10% sodium hydroxide. The mixture is then made acidic with aqueous 2N hydrochloric acid. The organic layer is separated and dried with magnesium sulfate. The mixture is filtered and concentrated under reduced pressure, yielding 41.7 grams of 2-methyl-2-(4-chlorophenyl)propanol. The NMR spectrum is consistent with the proposed structure.

Workup

  1. temperatureis cooled in an ice-water bath
  2. additionUpon completion of addition
  3. temperatureAfter this time the reaction mixture is cooled in an ice-water bath
  4. customthe reaction is quenched with the careful dropwise addition of water
  5. additionUpon completion of addition
  6. additionthe reaction mixture is made basic with the slow addition of aqueous 10% sodium hydroxide
  7. customThe organic layer is separated
  8. dry with materialdried with magnesium sulfate
  9. filtrationThe mixture is filtered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c2c43eb3eca74d37bfd916f057e1e68c
Source dataset
uspto-grants-1997_04
Patent number
US05622954

Reaction notes

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