Glycolaldehyde → HCID 54195334, compound

HRID 1296853Notes

Reaction equation

HRID 1296853 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:6])[CH3:2].[CH2:27](O)[CH:28]=[O:29]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:26])[C:5]([CH3:6])=[CH:27][CH2:28][OH:29])[CH3:2]

Participants

4

Reactant 2

HCID 756GlycolaldehydeHCID 79792Ethyl 2-(triphenylphosphoranylidene)propionate

Product 1

HCID 54195334HCID 54195334, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

886 g (2.44 mol) of 2-(triphenyl-phosphanylidene)-propionic acid ethyl ester in methylene chloride (4 L) was added dropwise into a refluxing solution of glycoaldehyde dimer (140 g, 1.17 mol) in methylene chloride (6 L). After refluxing for 4 h, the solvent was evaporated. Resulting crude product was fractionated (bp 108–114° C. at 2 mmHg) to give 304 g (90%) pure product as an oil. 1H-NMR (300 Hz CDCl3) δ 6.88 (t, 1H, CH), 4.35 (d, 2H, CH2OH), 4.20 (q, 2H, OCH2), 1.85 (s, 3H, CH3), 1.30 (t, 3H, CH3).

Workup

  1. temperatureAfter refluxing for 4 h
  2. customthe solvent was evaporated
  3. customResulting crude product

Sources & evidence

ORD record
ord-42caa10c75324d96beef2c61f12522fd
Source dataset
uspto-grants-2007_07
Patent number
US07247752B2

Reaction notes

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