Hydroquinone → Pidobenzone

HRID 260240Notes

Reaction equation

HRID 260240 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8].[C:10]1([CH:17]=[CH:16][C:14](O)=[CH:13][CH:12]=1)[OH:11]>O>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([O:9][C:14]1[CH:16]=[CH:17][C:10]([OH:11])=[CH:12][CH:13]=1)=[O:8]

Participants

4

Reactant 2

HCID 785HydroquinoneHCID 7405L-Pyroglutamic Acid

Product 1

HCID 3047843Pidobenzone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

129 g (1 mol) of (l)-pyroglutamic acid and 110 g (1 mol) of hydroquinone are intimately mixed, the mixture is stirred at 175° under a stream of nitrogen for 18 hours, the temperature is lowered to 50° and the mixture is diluted with water (300 ml) and extracted with ethyl acetate (3×400 ml). A crude product is thus prepared which is purified by being made into a paste twice with ethyl acetate (250 ml) to give the title derivative in the form of crystals melting at 179°/82°. In TLC, the product shows a single spot of Rf(i)=0.33.

Workup

  1. customis lowered to 50°
  2. extractionextracted with ethyl acetate (3×400 ml)
  3. customA crude product is thus prepared which
  4. customis purified

Sources & evidence

ORD record
ord-adb5b6779d3b417cba31e8c04cc22d77
Source dataset
uspto-grants-1996_06
Patent number
US05527523

Reaction notes

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