Glycolic Acid → HCID 22337743, compound
Reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].[Br:6][CH2:7][CH2:8][CH2:9]Br.[H-].[Na+]>C1COCC1>[Br:6][CH2:7][CH2:8][CH2:9][O:3][CH2:2][C:1]([OH:5])=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of glycolic acid (2.03 g, 26 mmol) and 1,3-dibromopropane (6.41 g, 32 mmol) in THF (50 ml) was added sodium hydride (1.56 g, 65 mmol). This was stirred at room temperature for 16 h. The reaction mixture was quenched with dilute HCl (1.0 M, 100 ml) and then extracted into chloroform (3×50 ml). This was then washed with brine, dried, filtered and evaporated to dryness in vacuo. The residue was purified by chromatography (SiO2, CHCl3 /MeOH) to yield the title compound (2.91 g, 57%).
Workup
- customThe reaction mixture was quenched with dilute HCl (1.0 M, 100 ml)
- extractionextracted into chloroform (3×50 ml)
- washThis was then washed with brine
- customdried
- filtrationfiltered
- customevaporated to dryness in vacuo
- customThe residue was purified by chromatography (SiO2, CHCl3 /MeOH)
Sources & evidence
- ORD record
- ord-f25ebd07ae114e5e9446a3931e9ebcc5
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06140494
Reaction notes
Loading…