Glycolic Acid → 2-Hydroxy-1-(pyrrolidin-1-yl)ethan-1-one

HRID 2420698Notes

Reaction equation

HRID 2420698 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6](O)(=[O:9])[CH2:7][OH:8]>CC1C=CC=CC=1C>[OH:9][CH2:6][C:7]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:8]

Participants

4

Reactant 2

HCID 757Glycolic AcidHCID 31268Pyrrolidine

Product 1

HCID 64804852-Hydroxy-1-(pyrrolidin-1-yl)ethan-1-oneYield 90%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

Pyrrolidine (3.0 mL; 35.9 mmol) was added to glycolic acid (2.73 g; 35.9 mmol) over 5 minutes while cooling in an ice bath. The suspension was diluted with o-xylene (3.5 mL) and heated to reflux for 7 h whereupon the o-xylene was removed by distillation to afford the title compound (4.17 g; 90%) as an orange oil. 1H NMR (CDCl3) δ 1.86-4.92 (m, 2H), 1.96-2.02 (m, 2H), 3.26-3.29 (m, 2H), 3.52-3.55 (m, 3H), 4.08 (s, 2H); 13C NMR (CDCl3) δ 23.94, 25.74, 44.26, 45.96, 60.48, 169.90.

Workup

  1. temperaturewhile cooling in an ice bath
  2. temperatureheated
  3. customwas removed by distillation

Sources & evidence

ORD record
ord-fa6f452ef79c47f38619c438160167e2
Source dataset
uspto-grants-2011_06
Patent number
US07956049B2

Reaction notes

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