Glyoxylic Acid → 3-Heptyl-4-oxo-2-pentenoic acid

HRID 968145Notes

Reaction equation

HRID 968145 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=O.[CH3:6][C:7](=[O:16])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>P(=O)(O)(O)O>[CH2:9]([C:8]([C:7](=[O:16])[CH3:6])=[CH:2][C:1]([OH:5])=[O:4])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 760Glyoxylic AcidHCID 127412-Decanone

Product 1

HCID 858009953-Heptyl-4-oxo-2-pentenoic acid

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

Prepared from glyoxylic acid (5.10 g, 6.7 mmol), 2-decanone (15.0 g, 9.6 mmol) and orthophosphoric acid (20 ml). νmax 2925, 2820, 1690, 1460, 1380, 1240, 1120, 880, 720 cm−1. 1H n.m.r. δ (CDCl3) 0.87, t J 7.2 Hz, 3H, CH3; 1.29, m, 10H, CH2; 2.39, s, 3H, CH3; 2.77, t J 6.8 Hz, 2H, CH2; 6.50, s, CH. 13C n.m.r. δ (CDCl3): 13.9, CH3; 22.5, 26.6, 26.9, 29.1, 29.6, 31.6 CH2; 28.8, CH3; 124.3, C2; 157.9, C3; 170.9, COOH; 199.9 C2.

Sources & evidence

ORD record
ord-c82b01cae41b4db5aecbbaf5007cfc22
Source dataset
uspto-grants-2005_10
Patent number
US06958145B2

Reaction notes

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