Oxalyl chloride → HCID 21069967, compound

HRID 1788103Notes

Reaction equation

HRID 1788103 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][O:5][CH:6]([CH3:10])[C:7]([OH:9])=[O:8].[C:11](Cl)(=O)C(Cl)=O>CO>[CH3:1][S:2][CH2:3][CH2:4][O:5][CH:6]([CH3:10])[C:7]([O:9][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 21069793HCID 21069793, compound

Product 1

HCID 21069967HCID 21069967, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reaction of intermediate 9, 2-(2-(methylthio)ethoxy)propanoic acid, (13.70 g, 0.083 mol) with oxalyl chloride followed by reaction with methanol gave 14.27 g (96% yield) of the title ester as a clear oil; bp 55-60° C./0.3 torr (bulb to bulb distillation, air bath temperature). 1HNMR 400 MHz (CDCl3) δ ppm: 1.42 (3H, d, J=7.0 Hz, CH3), 2.15 (3H, s, SCH3), 2.71 (2H, t, J=6.8 Hz, CH2), 3.56 (1H, m, CH), 3.75 (3H, s, OCH3), 3.78 (1H, m, CH), 4.15 (1H, q, J=7.0 Hz, OCH).

Sources & evidence

ORD record
ord-8e961f4262fe4f58bd3081ac9c1db85e
Source dataset
uspto-grants-2009_03
Patent number
US07511037B2

Reaction notes

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