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

HRID 1271799Notes

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-27b49610ea7745b9a40dec43bcfae098
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208145B2

Reaction notes

Loading…