Ammonium Acetate → N-(4-Hydroxyphenyl)glycine

HRID 1703061Notes

Reaction equation

HRID 1703061 reaction equation
O.[OH:2][C:3]1[CH:13]=[CH:12][C:6](C(O)C([O-])=O)=[CH:5][CH:4]=1.[Na+].[C:15]([O-:18])(=[O:17])[CH3:16].[NH4+:19]>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([NH:19][CH2:16][C:15]([OH:18])=[O:17])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 236981332-Hydroxy-2-(4-hydroxyphenyl)acetic acid, sodium salt hydrate

Product 1

HCID 67149N-(4-Hydroxyphenyl)glycineYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
125 °C

Procedure

A mixture of sodium p-hydroxymandelate monohydrate (1.04 g.), ammonium acetate (2.0 g.) and water (0.5 ml.) is stirred and heated under reflux (internal temperature 125° C.) for 2.5 hours. Water (3 ml.) is added to the thick slurry thus obtained, the mixture is cooled and filtered and the solid residue is washed twice with water and then with acetone. There is thus obtained p-hydroxyphenylglycine (0.56 g., 66% yield).

Workup

  1. temperatureheated
  2. customthus obtained
  3. temperaturethe mixture is cooled
  4. filtrationfiltered
  5. washthe solid residue is washed twice with water

Sources & evidence

ORD record
ord-5199c7298b8e4d23b317a13a977cf9e7
Source dataset
uspto-grants-1982_09
Patent number
US04350826

Reaction notes

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