Hydrochloric Acid → 2-[4-(4-Chlorophenoxy)-phenoxy]-propanol

HRID 263077Notes

Reaction equation

HRID 263077 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:18]=[CH:17][C:10]([O:11][CH:12]([CH3:16])[C:13](O)=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[H-].Cl>C(OCC)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:18]=[CH:17][C:10]([O:11][CH:12]([CH3:16])[CH2:13][OH:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 64928ClofopHCID 166653HydrideHCID 21226445Aluminium lithium hydride

Product 1

HCID 128048842-[4-(4-Chlorophenoxy)-phenoxy]-propanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 22.5 g (0.077 mol) of (±)-2-[4-(4-chlorophenoxy)-phenoxy]-propionic acid (CRL 40299) in 150 ml of anhydrous diethyl ether is run over the course of 1 hour 30 minutes into a suspension of 6.6 g (0.173 mol) of LiAlH4 in 50 ml of anhydrous diethyl ether. Thereafter the reflux is maintained for 1 hour 30 minutes, the excess hydride is neutralised with ethyl acetate and the complex is hydrolysed with dilute hydrochloric acid. The organic phase is decanted, washed with water and dilute sodium hydroxide solution and gives, after drying over dry sodium sulphate and evaporation of the solvent, 21.4 g of a crystalline white mass, which is insoluble in water.

Workup

  1. temperatureThereafter the reflux is maintained for 1 hour 30 minutes
  2. customThe organic phase is decanted
  3. washwashed with water and dilute sodium hydroxide solution
  4. customgives
  5. dry with materialafter drying over dry sodium sulphate and evaporation of the solvent, 21.4 g of a crystalline white mass, which

Sources & evidence

ORD record
ord-5332fa105e0b48e7834e8392b8d3f779
Source dataset
uspto-grants-1979_05
Patent number
US04156011

Reaction notes

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