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

HRID 2058093Notes

Reaction equation

HRID 2058093 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([NH:6][CH2:7][C:8]2[CH:21]=[CH:20][C:11]([O:12][CH:13]([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:23]=[CH:22][C:5]([NH:6][CH2:7][C:8]2[CH:21]=[CH:20][C:11]([O:12][CH:13]([CH3:19])[CH2:14][OH:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 20329856Ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]propionateHCID 21226445Aluminium lithium hydride

Product 1

HCID 203298502-{4-[(4-Chloroanilino)methyl]phenoxy}propan-1-olYield 81.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2.0 g of ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]propionate in 20 ml of ether is dropwise added to a suspension of 324 mg of lithium aluminum hydride in 20 ml of anhydrous ether over a period of 10 minutes under 10° C. The mixture is stirred for 20 minutes at room temperature and cooled under 10° C., and to the mixture is dropwise added 25 ml of 10% ammonium chloride aqueous solution. An insoluble material is filtered off and the ether layer is separated. The aqueous layer is extracted with ether and both of the ether layers are combined. The extract is washed with a saturated sodium chloride aqueous solution and dried, after which the solvent is distilled off. The residue is collected by filtration, washed with a mixture of n-hexane and diisopropyl ether and dried to give 1.42 g of 2-[4-(4-chloroanilinomethyl)phenoxy]propanol, mp 81° to 83° C.

Workup

  1. temperaturecooled under 10° C.
  2. filtrationAn insoluble material is filtered off
  3. customthe ether layer is separated
  4. extractionThe aqueous layer is extracted with ether
  5. washThe extract is washed with a saturated sodium chloride aqueous solution
  6. customdried
  7. distillationafter which the solvent is distilled off
  8. filtrationThe residue is collected by filtration
  9. washwashed with a mixture of n-hexane and diisopropyl ether
  10. customdried

Sources & evidence

ORD record
ord-579984e020674d7bbb8c506b7e7d665b
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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