Glyoxylic Acid → HCID 18620256, compound

HRID 430727Notes

Reaction equation

HRID 430727 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].[C:13](O)(=[O:16])[CH:14]=[O:15]>ClCCCl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([C:5]1[C:6]2[O:12][C:14](=[O:15])[CH:13]([OH:16])[C:7]=2[CH:8]=[C:9]([Cl:11])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 760Glyoxylic Acid2×HCID 5187652-(tert-Butyl)-4-chlorophenol

Product 1

HCID 18620256HCID 18620256, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

2.8 g of 2-tert-butyl-4-chlorophenol [J. Amer. Chem. Soc. 78, 4604 (1956)] are refluxed for 3¼ h with 2.45 g of 50% aqueous glyoxylic acid and 50 mg of p-toluenesulfonic acid in 20 ml of 1,2-dichloroethane. Thereafter a further 2.45 g of 50% aqueous glyoxylic acid are added to continue refluxing for 18 h. The reaction mixture is then washed with water, dried over MgSO4 and evaporated in a rotary evaporator. Crystallization of the residue from hexane leaves 1.15 g of 7-tert-butyl-5-chloro-3-hydroxy-3H-benzofuran-2-one (melting point: 150-154° C.).

Workup

  1. temperatureto continue refluxing for 18 h
  2. washThe reaction mixture is then washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated in a rotary evaporator
  5. customCrystallization of the residue from hexane

Sources & evidence

ORD record
ord-0e058f2e105b4405b7e6b191381a9946
Source dataset
uspto-grants-2001_11
Patent number
US06323267B1

Reaction notes

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