Glycine → N-[(2,4-dihydroxyphenyl)ethylidene]glycine

HRID 504070Notes

Reaction equation

HRID 504070 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[OH:11])=O.[NH2:12][CH2:13][C:14]([OH:16])=[O:15]>O>[OH:11][C:5]1[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=1[CH2:2][CH:1]=[N:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 750GlycineHCID 69902',4'-Dihydroxyacetophenone

Product 1

HCID 25141972N-[(2,4-dihydroxyphenyl)ethylidene]glycine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Ingredients. (1) Water 97.5 (2) Resacetophenone 1.5 (3) Glycine 1.0. Procedure. The mixture of all ingredients is heated at 90 to 95 C for 2 hours. A solution of N-[(2,4-dihydroxyphenyl)ethylidene]glycine in water is obtained. It is then hydrogenated over platinum (Pt) catalyst, filtered, and then acidified to pH 6.5. [RS]-N-[(2,4-dihydroxyphenyl)ethyl]glycine is thus obtained, which is then resolved into the corresponding [R] and [S] optical isomers, and used directly in cosmetic compositions of the present invention.

Workup

  1. additionThe mixture of all ingredients
  2. temperatureis heated at 90 to 95 C for 2 hours

Sources & evidence

ORD record
ord-d3a5416a88724ccca0c1ff98f72ea503
Source dataset
uspto-grants-2010_08
Patent number
US07777073B2

Reaction notes

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