Ammonium Chloride → 2-{4-[(4-Chloroanilino)methyl]phenoxy}-2-methylpropan-1-ol

HRID 2058094Notes

Reaction equation

HRID 2058094 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([NH:6][CH2:7][C:8]2[CH:22]=[CH:21][C:11]([O:12][C:13]([CH3:20])([CH3:19])[C:14](OCC)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>CCOCC>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([NH:6][CH2:7][C:8]2[CH:22]=[CH:21][C:11]([O:12][C:13]([CH3:20])([CH3:19])[CH2:14][OH:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 20329838Ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]-2-methylpropionateHCID 21226445Aluminium lithium hydride

Product 1

HCID 203298702-{4-[(4-Chloroanilino)methyl]phenoxy}-2-methylpropan-1-olYield 79.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 5 g of ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]-2-methylpropionate in 50 ml of ether is dropwise added to a suspension of 775 mg of lithium aluminum hydride in 50 ml of anhydrous ether under 10° C. with stirring and the mixture is stirred for 2 hours at the same temperature. To the resultant mixture is dropwise added 60 ml of 10% ammonium chloride aqueous solution at 5° to 10° C. An insoluble material is filtered off and the ether layer is separated. The aqueous layer is further extracted with ether and both of the ether layers are combined. The combined ether solution is washed with a saturated sodium chloride aqueous solution and dried. The solvent is distilled off and the residue is washed with diisopropyl ether and dried to give 3.5 g of 2-[4-(4-chloroanilinomethyl)phenoxy]-2-methylpropanol, mp 84° to 91° C. This material is recrystallized from diisopropyl ether to give pure compound, mp 92° to 93° C.

Workup

  1. stirringthe mixture is stirred for 2 hours at the same temperature
  2. customat 5° to 10° C
  3. filtrationAn insoluble material is filtered off
  4. customthe ether layer is separated
  5. extractionThe aqueous layer is further extracted with ether
  6. washThe combined ether solution is washed with a saturated sodium chloride aqueous solution
  7. customdried
  8. distillationThe solvent is distilled off
  9. washthe residue is washed with diisopropyl ether
  10. customdried

Sources & evidence

ORD record
ord-3890966596c44d7a98748363106564c6
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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