Thionyl Chloride → 4-Acetoxy-3,5-dimethoxybenzoyl chloride

HRID 273453Notes

Reaction equation

HRID 273453 reaction equation
[C:1]([O:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2].S(Cl)([Cl:20])=O>C(COC)OC>[C:1]([O:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:8]([C:9]([Cl:20])=[O:10])=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 225680Acetyl syringic acid

Product 1

HCID 973074-Acetoxy-3,5-dimethoxybenzoyl chlorideYield 102.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Acetoxy-3,5-dimethoxy-benzoic acid (1.45 g) was heated with thionyl chloride (0.86 g) in 3 mL of dimethoxyethane. After 1.5 hours the mixture was stripped under vacuum leaving 1.60 g of 4-acetoxy-3,5-dimethoxy-benzoyl chloride as an oil. 1H NMR (CDCl3, 300 MHz) δ (ppm): 2.26 (s, 3H), 3.89 (s, 9H), 7.34 (s, 2H).

Sources & evidence

ORD record
ord-4137546c85d445418b446ac2a16e3431
Source dataset
uspto-grants-2008_11
Patent number
US07456315B2

Reaction notes

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