Glycolic Acid → HCID 22337743, compound

HRID 370278Notes

Reaction equation

HRID 370278 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

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

  1. customThe reaction mixture was quenched with dilute HCl (1.0 M, 100 ml)
  2. extractionextracted into chloroform (3×50 ml)
  3. washThis was then washed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo
  7. 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

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