Ammonium Chloride → (5-Amino-2-chlorophenyl)methanol

HRID 2371778Notes

Reaction equation

HRID 2371778 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>>[Cl:11][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:10][C:6]=1[CH2:7][OH:8]

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 378795-Amino-2-chlorobenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 13567962(5-Amino-2-chlorophenyl)methanolYield 52.7%

Procedure

Under an inert atmosphere, 300 g of lithium aluminum hydride is provided in 3 1 of tetrahydrofran at 0° C. and treated in portions with 500 g of 5-amino-2-chlorobenzoic acid nindustrial, 85%). Thereafter the reaction mixture is heated slowly to room temperature and stirred over night at this temperature. For further processing the reaction mixture is cooled to 0° C. and the excessive lithium aluminum hydride is carefuly decomposed with saturated ammonium chloride solution. Thereafter the organic phase is separated from the deposit and this deposit is washed several times with acetic ester and methylene chloride. The united organic phases are washed neutral with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. A yield of 242 g of crude 2-chloro-5-aminobenzyl alcohol is obtained the purity of which is adequate for subsequent reactions.

Workup

  1. temperatureFor further processing the reaction mixture is cooled to 0° C.
  2. customThereafter the organic phase is separated from the deposit
  3. washthis deposit is washed several times with acetic ester and methylene chloride
  4. washThe united organic phases are washed neutral with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dccc159e2248433d8bb63d0b7d317e52
Source dataset
uspto-grants-1992_03
Patent number
US05095129

Reaction notes

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