Glyoxylic Acid → HCID 11264022, compound
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=[O:12].C1(C(=CC(=CC=1)C)C)C.C(O)(=O)C=[O:25]>>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[CH:10]([OH:25])[C:11]([OH:13])=[O:12]Participants
Procedure
Finally, a further possibility for preparing 2,4,5-trimethylphenylacetic acid is to initially react pseudocumene with glyoxylic acid to give 2,4,5-trimethylmandelic acid (Atti Accad., Lettere Arti Palermo, Pt. I24 (1965) 19–33) and then to reduce it to 2,4,5-trimethylphenylacetic acid (J. Amer. Chem. Soc. 58 (1936) 629–35). However, the preparation of 2,4,5-trimethylmandelic acid by the process specified has the disadvantage that the 2,4,5-trimethylmandelic acid which has already formed reacts with further pseudocumene under the customary reaction conditions and thus forms considerable proportions of 2,2′,4,4′,5,5′-hexamethyldiphenylacetic acid (Atti Accad., Lettere Arti Palermo, Pt. I24 (1965) 19–33), which of course reduce the yield and make necessary additional purification steps.
Sources & evidence
- ORD record
- ord-8f12bd21743144a5978d304db29bdb49
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07019166B2
Reaction notes
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