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Toluene → 2-(1,3,5-Triethylphenyl)-2-oxoacetyl chloride

HRID 579246
Notes
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Reaction equation

HRID 579246 reaction equation
[CH2:1]([C:3]1([C:13](=[O:17])[C:14](O)=[O:15])[CH:8]=[C:7]([CH2:9][CH3:10])[CH:6]=[C:5]([CH2:11][CH3:12])[CH2:4]1)[CH3:2].C1(C)C=CC=CC=1.S(Cl)([Cl:27])=O>CN(C)C=O>[CH2:1]([C:3]1([C:13](=[O:17])[C:14]([Cl:27])=[O:15])[CH:8]=[C:7]([CH2:9][CH3:10])[CH:6]=[C:5]([CH2:11][CH3:12])[CH2:4]1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 666915612-(1,3,5-Triethylphenyl)-2-oxoacetic acid

Product 1

HCID 866893512-(1,3,5-Triethylphenyl)-2-oxoacetyl chlorideYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a 3 L volume four-necked flask, 2-(1,3,5-triethylphenyl)-2-oxoacetic acid (8-b) (214.8 g), toluene (anhydrous) (740 ml), and dimethylformamide (anhydrous) (22.8 ml) were added under a nitrogen atmosphere. After the temperature was raised to about 50° C. thionyl chloride (131 g) was added. The resulting mixture was stirred at 50° C. for 2 hours, and concentrated under reduced pressure to give 204.5 g of 2-(1,3,5-triethylphenyl)-2-oxoacetyl chlorine (6-b).

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da10d8d35cb84777b957f514f0fe7f74
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040709B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes