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Oxalyl chloride → 2-(3,4,5-trimethoxyphenyl)acetyl Chloride

HRID 343685
Notes
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Reaction equation

HRID 343685 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][C:14]([OH:16])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(Cl)(=O)C([Cl:20])=O>CN(C)C=O.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][C:14]([Cl:20])=[O:16])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 703723,4,5-Trimethoxyphenylacetic acid

Product 1

HCID 110321242-(3,4,5-trimethoxyphenyl)acetyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

Combine 3,4,5-trimethoxy-phenyl-acetic acid (2.26 g, 10 mmol) and dichloromethane (50 mL). Cool to -5° C. using a ice-salt bath. Add 2 drops of dimethylformamide followed by dropwise addition of oxalyl chloride (1.74 mL, 20 mmol). after 1 hour, warm the reaction mixture to ambient temperature. After 2 hours, evaporate the reaction mixture in vacuo to give the title compound as a liquid.

Workup

  1. temperaturewarm the reaction mixture to ambient temperature
  2. waitAfter 2 hours
  3. customevaporate the reaction mixture in vacuo

Sources & evidence

ORD record
ord-6016ca57d90b42e6bab08cf26c2c315b
Source dataset
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05861416

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes