Hydroxyphenylacetic acid → HCID 10633141, compound

HRID 1704096Notes

Reaction equation

HRID 1704096 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1.Br[CH2:15][CH2:16][CH2:17][Cl:18]>C(O)C>[Cl:18][CH2:17][CH2:16][CH2:15][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 80061-Bromo-3-chloropropaneHCID 14797Potassium Hydroxide

Product 1

HCID 10633141HCID 10633141, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 41 g of potassium hydroxide in 250 ml of ethanol is added 50 g of p-hydroxyphenylacetic acid. To this solution is added 32 ml of 3-bromo-1-chloropropane and the mixture is refluxed for 4 hours. The mixture is cooled in an ice bath and filtered. The filtrate is acidified to pH 2 with concentrated HCl. Filtration gives a solid which is washed with water to give 68 g of product. Recrystallization from acetic acid water gives white crystals, mp 89°-91° C.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. temperatureThe mixture is cooled in an ice bath
  3. filtrationfiltered
  4. filtrationFiltration
  5. customgives a solid which
  6. washis washed with water

Sources & evidence

ORD record
ord-1ab371e2adfb4fba9689f027d5c6d221
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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