Glyoxylic Acid → HCID 22057561, compound

HRID 1828660Notes

Reaction equation

HRID 1828660 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([CH2:15][CH3:16])([CH3:14])[CH3:13])[C:7]=1O)([CH2:4][CH3:5])([CH3:3])[CH3:2].[C:18]([OH:22])(=[O:21])[CH:19]=[O:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C(Cl)CCl>[C:1]([C:6]1[CH:7]=[C:8]([C:12]([CH2:15][CH3:16])([CH3:14])[CH3:13])[C:9]2[O:22][C:18](=[O:21])[CH:19]([OH:20])[C:10]=2[CH:11]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 760Glyoxylic AcidHCID 6101p-Toluenesulfonic acidHCID 144965062,6-Di-tert-pentylphenol

Product 1

HCID 22057561HCID 22057561, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

2,6-Di-tert-pentylphenol (161.4 g), glyoxylic acid (122.3 g of the 50% b.w. solution in water) and 1.3 g of p-toluene sulphonic acid are heated in 500 ml of ethylenechloride under nitrogen at reflux temperature in an apparatus designed for the removal of water. After 3.5 hours the reaction mixture is cooled to room temperature, washed 3 times with 25 ml water, dried over magnesium sulphite and evaporated under reduced pressure to give 214.3 g of: 5,7-di-tert-pentyl-3-hydroxy-3H-benzofuran-2-one as an orange coloured oil.

Workup

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

Sources & evidence

ORD record
ord-25eea8fcf0c948a78fe7e79e6edb23a3
Source dataset
uspto-grants-2006_06
Patent number
US07060425B1

Reaction notes

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