Oxalic Acid → Ethyl 1-formylcyclopropanecarboxylate

HRID 512134Notes

Reaction equation

HRID 512134 reaction equation
C(O)(=O)[C:2](O)=[O:3].[CH2:7]([O:9][C:10]([CH:12]1[CH2:14][CH2:13]1)=[O:11])[CH3:8]>O>[CH2:7]([O:9][C:10]([C:12]1([CH:2]=[O:3])[CH2:14][CH2:13]1)=[O:11])[CH3:8]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 78351Ethyl cyclopropanecarboxylate

Product 1

HCID 9964122Ethyl 1-formylcyclopropanecarboxylateYield 51.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Oxalic acid (11.2 g, 0.124 mol) was dissolved in water (40 mL) and 144,4,6-trimethyl-[1,3]oxazinan-2-yl)-cyclopropanecarboxylic acid ethyl ester (15 g, 0.062 mol) was added. Steam distillation of this mixture was carried out until 500 mL of distillate had been collected. The distillate was saturated with NaCl and extracted with EtOAc (2×100 mL). The organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give 1-formyl-cyclopropanecarboxylic acid ethyl ester (4.5 g, 51%). 1H NMR (CDCl3 400 MHz): δ10.39 (s, 1H), 4.26 (q, J=7.2 Hz, 2H), 1.67-1.64 (m, 2H), 1.61-1.58 (m, 2H), 1.31 (t, J=7.2 Hz, 3H).

Workup

  1. distillationSteam distillation of this mixture
  2. customhad been collected
  3. extractionextracted with EtOAc (2×100 mL)
  4. dry with materialThe organic extracts were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bba7275d0f724c03909036c810a95976
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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