Dimethylformamide → 4-Acetoxy-3-methoxybenzoyl chloride

HRID 2298607Notes

Reaction equation

HRID 2298607 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[O:14][CH3:15])(=[O:3])[CH3:2].C(Cl)(=O)C([Cl:19])=O.CN(C=O)C>C(Cl)Cl>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:19])=[O:10])=[CH:7][C:6]=1[O:14][CH3:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 66346Benzoic acid, 4-(acetyloxy)-3-methoxy-

Product 1

HCID 924974-Acetoxy-3-methoxybenzoyl chlorideYield 103%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 1.00 g (4.76 mmol) of 4-acetoxy-3-methoxybenzoic acid (Pfaltz and Bauer, Inc.) in 4 mL of anhyd CH2Cl2 (under a CaSO4 drying tube) was added 4.15 mL (47.6 mmol) of oxalyl chloride followed by 25 μL of anhyd DMF. After stirring for 4 h at room temperature, the mixture was concentrated in vacuo to afford the title compound as light yellow crystals (1.12 g, 103%). 1H-NMR (300 MHz, CDCl3) δ7.81 (dd, 1H, J=8.4, 2.1 Hz), 7.66 (d, 1H, 2.1 Hz), 7.19 (d, 1H, 8.4 Hz), 3.91 (s, 3H), and 2.35 (s, 3H).

Workup

  1. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-99e131b80764478d88e138da5526c802
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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