Glyoxylic Acid → HCID 11833211, compound

HRID 1828662Notes

Reaction equation

HRID 1828662 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=1.[C:18](O)(=[O:21])[CH:19]=[O:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C(Cl)CCl>[C:13]([C:8]1[C:9]2[O:12][C:19](=[O:20])[CH:18]([OH:21])[C:10]=2[CH:11]=[C:6]([CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:17])[CH:7]=1)([CH3:14])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 760Glyoxylic AcidHCID 6101p-Toluenesulfonic acidHCID 3084638Benzenepropanoic acid, 3-(1,1-dimethylethyl)-4-hydroxy-, methyl ester

Product 1

HCID 11833211HCID 11833211, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

3-(4-hydroxy-3-tert.butylphenyl) propionic acid methyl ester (10.0 g), glyoxylic acid (7.4 g of the 50% solution in water) and p-toluene sulphonic acid (40 mg) are heated in 40 ml ethylene chloride under nitrogen at reflux for 3 hours distilling off all water present and formed during the reaction. The reaction mixtures is washed with water, dried over magnesium sulphate and evaporated under reduced pressure to give 13.0 g of 7-tert.butyl-5-(2-methoxycarbonylethyl)-3-hydroxy-3H-benzofuran-2-one.

Workup

  1. temperatureat reflux for 3 hours
  2. distillationdistilling off all water present
  3. customformed during the reaction
  4. customThe reaction mixtures
  5. washis washed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-688995f89988411e96f1dd18517701b3
Source dataset
uspto-grants-2006_06
Patent number
US07060425B1

Reaction notes

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