Triethylamine → 3-Methyl-6-hexyl-1,4-dioxane-2,5-dione
Reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([OH:5])=[O:4].Br[CH:13]([CH3:17])[C:14](Br)=[O:15].C(N(CC)CC)C>CC(C)=O>[CH3:17][CH:13]1[O:4][C:3](=[O:5])[CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[O:1][C:14]1=[O:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
2.5 g 2-hydroxyoctanoic acid (15.6 mmol) and 1.75 mL 2-bromopropionyl bromide (16.3 mmol) were stirred at 80° C. under nitrogen for 12 h. 150 mL acetone and 4.35 mL anhydrous triethylamine (31 mmol) were added to the mixture and the solution was stirred for 3 h at 60° C. After filtration of the triethylammonium bromide salts, acetone was distilled off and the resulting mixture was dissolved in 250 mL ethyl acetate:hexane mixture (1:2). After filration over silica gel the solvents were distilled off, and the remaining crude product was recrystallized from hexane. 1H NMR (500 MHz, CDCl3): δ 5.00 (q, 1H), 4.89 (dd, 1H), 1.9-2.15 (br m, 2H), 1.70 (d), 1.66 (d), (3H, of 2 diastereoisomers), 1.45-1.65 (br m, 2H), 1.25-1.40 (br m, 6H), 0.90 (t, 3H). 13C NMR (500 MHz, CDCl3): δ 167.53, 166.90. 166.26, 165.87, 75.80, 72.49, 72.25, 31.92, 31.45, 31.39, 30.00, 28.73, 28.50, 24.60, 24.29, 22.48, 22.44, 17.54, 15.83, 14.00. ELEM. ANAL. Calcd. for C11H18O4: C, 61.68; H, 8.41. Found: C, 61.63; H, 8.48. Yield: 45%.
Workup
- filtrationAfter filtration of the triethylammonium bromide salts, acetone
- distillationwas distilled off
- dissolutionthe resulting mixture was dissolved in 250 mL ethyl acetate
- distillationAfter filration over silica gel the solvents were distilled off
- customthe remaining crude product was recrystallized from hexane
Sources & evidence
- ORD record
- ord-7afba8678b0e43d0b09b21bb936e979b
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09375482B2
Reaction notes
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