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

HRID 504075Notes

Reaction equation

HRID 504075 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][NH:11][CH2:12][C:13]([OH:15])=[O:14].C1C(O)=CC=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=1>O>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH:10]=[N:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 440936ArbutinHCID 25141840HCID 25141840, compound

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 Ni 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. Both the [R,S] and [R] and [S] compounds thus obtained are esterified with methanol/thionyl chloride method to the corresponding methyl esters, which are 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-7bafc27119184dd69684a6e93f6b7ca9
Source dataset
uspto-grants-2010_08
Patent number
US07777073B2

Reaction notes

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