Glyoxylic Acid → HCID 22057549, compound

HRID 1828661Notes

Reaction equation

HRID 1828661 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][CH2:6][C:7]([CH3:19])([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:16]([CH3:18])[CH3:17])[CH:10]=1)[CH3:8].[C:21](O)(=[O:24])[CH:22]=[O:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C(Cl)CCl>[CH:16]([C:11]1[C:12]2[O:15][C:22](=[O:23])[CH:21]([OH:24])[C:13]=2[CH:14]=[C:9]([C:7]([CH3:19])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:20])[CH:10]=1)([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 760Glyoxylic AcidHCID 6101p-Toluenesulfonic acidHCID 19864970HCID 19864970, compound

Product 1

HCID 22057549HCID 22057549, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

5-Methyl-5-(4-hydroxy-3-isopropyl phenyl)-hexanoic acid methyl ester (10.0 g), glyoxylic acid (6.4 g of the 50% solution in water) and p-toluene sulphonic acid (40 mg) are heated in 40 ml of ethylene chloride under nitrogen at reflux in an apparatus designed for the removal of water. After 5 hours the reaction mixture is cooled to room temperature, washed two times with 25 ml water, dried over magnesium sulphate and evaporated under reduced pressure to give 13 g of 7-isopropyl-5-(4-methoxycarbonyl-1,1-dimethylbutyl)-3-hydroxy-3H-benzofuran-2-one as a yellow oil.

Workup

  1. temperatureat reflux in an apparatus
  2. customdesigned for the removal of water
  3. washwashed two times with 25 ml water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0b47499095654387935fe03293fa9837
Source dataset
uspto-grants-2006_06
Patent number
US07060425B1

Reaction notes

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