Glyoxylic Acid → HCID 10012697, compound

HRID 1669116Notes

Reaction equation

HRID 1669116 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:11]([OH:15])(=[O:14])[CH:12]=O>O1CCOCC1>[O:10]=[C:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]/[C:2]/1=[CH:12]\[C:11]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 760Glyoxylic AcidHCID 67351-Indanone

Product 1

HCID 10012697HCID 10012697, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-indanone (145) (25 g, 190 mmol), glyoxylic acid (50% aqueous solution, 70 g, 470 mmol), and CH2SO4 (6.25 mL) in dioxane (25 mL) were stirred at reflux temperature for 4 h. The mixture was cooled, the product filtered off, washed with water and dried to give acid 146 (32.8 g, 92%) as a white solid: mp 201-203° C. [lit. (Nagasawa et al., Japanese Patent 04338358, 1992) 205-206° C.]; 1H NMR [(CD3)2SO] δ 12.00 (br s, 1H, OH), 7.73-7.80 (m, 2H, H-5, H-7), 7.68 (br d, J=7.7 Hz, 1H, H-4), 7.49 (t, J=7.9 Hz, 1H, H-6), 6.55 (t, J=2.4 Hz, 1H, CHCO2), 4.08 (d, J=1.8 Hz, 2H, H-3).

Workup

  1. temperatureat reflux temperature for 4 h
  2. temperatureThe mixture was cooled
  3. filtrationthe product filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2a0a0156d5b64aacb0ce4b1cea1a68f7
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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