Sodium Carbonate → Propionic acid, 2,2-diethoxy-, ethyl ester

HRID 537648Notes

Reaction equation

[C:1]([O:6][CH2:7][CH3:8])(=[O:5])C(C)=O.[CH:9]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])OCC.[C:19]([O-])([O-])=O.[Na+].[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)C>[CH2:17]([O:16][C:9]([O:13][CH2:14][CH3:15])([CH3:19])[C:1]([O:6][CH2:7][CH3:8])=[O:5])[CH3:18]

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of ethyl pyruvate (13.92 g, 0.120 moles), triethyl orthoformate (19.44 g, 0.131 moles), ethyl alcohol (9.0 g), and p-toluenesulfonic acid monohydrate (0.0432 g, 0.00227 moles) was stirred at 45° C. overnight under nitrogen atmosphere. Next, after cooling to room temperature, Na2CO3 (1.20 g) was added and the mixture was stirred for 15 minutes. The reaction mixture was then filtered and ethyl alcohol and residual triethyl orthoformate were distilled off under reduced pressure. The residue was subjected to fractional vacuum distillation giving 18.2 g of pure ethyl pyruvate diethyl ketal. NMR (d6-DMSO): 1.27 ppm (t, —CH3, ethyl (ketal), 6H) 1.34 ppm (t, —CH3, ethyl (ester), 3H), 1.40 ppm (s, —CH3—C—COO—, 3H), 3.45 ppm (q, —OCH2CH3, (ketal), 4H), 4.29 ppm (q, —OCH2CH3, (ester), 2H).

Workup

temperatureNext, after cooling to room temperature
stirringthe mixture was stirred for 15 minutes
filtrationThe reaction mixture was then filtered
distillationethyl alcohol and residual triethyl orthoformate were distilled off under reduced pressure
distillationThe residue was subjected to fractional vacuum distillation

Sources & evidence

ORD record: ord-7c90bc686a21480e84fdddea154fee4c
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865149B2

Reaction notes

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