2-Hydroxybutyric Acid → HCID 12037227, compound

HRID 992662Notes

Reaction equation

HRID 992662 reaction equation
[OH:1][CH:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].Br[CH:9]([CH3:13])[C:10](Br)=[O:11]>>[CH2:6]([CH:2]1[C:3](=[O:5])[O:4][CH:9]([CH3:13])[C:10](=[O:11])[O:1]1)[CH3:7]

Participants

3

Reactant 2

HCID 112662-Hydroxybutyric AcidHCID 79047Propanoyl bromide, 2-bromo-

Product 1

HCID 12037227HCID 12037227, compoundYield 53%

Procedure

3-ethyl-6-methyl-2,5-dioxane-1,4-dione was synthesized from 2-hydroxybutyric acid and 2-bromopropionyl bromide. It was purified by distillation (45° C./50 mtorr) to give a colorless oil. Yield: 53% 1H NMR (CDCl3) δ5.03 (q), 4.99 (q, 1H for signal at 5.03 and 4.99 ppm), 4.86 (dd), 4.83 (dd, 1H for signal at 4.86 and 4.83), 1.90-2.20 (m, 2H), 1.69 (d), 1.66 (d, 3H for signals at 1.69 and 1.66 ppm). 1.15 (t). 1.14 (t, 3H for signals at 1.15 and 1.14 ppm). 13C NMR (CDCl3) δ167.6, 166.8, 166.3, 165.6, 77.7, 76.6, 72.5, 72.2, 25.3, 23.3, 17.5, 15.7, 9.1, 8.7, MS (m/q) 159.4 (M+1). The product is approximately a 3:1 mixture of the R,R/S,S and R,S diastereomers.

Workup

  1. distillationIt was purified by distillation (45° C./50 mtorr)
  2. customto give a colorless oil
  3. additiona 3:1 mixture of the R,R/S,S and R,S diastereomers

Sources & evidence

ORD record
ord-cc240d3accd84d76ac3fc397b1a702b2
Source dataset
uspto-grants-2002_10
Patent number
US06469133B2

Reaction notes

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