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2-Chlorobenzoyl chloride → HCID 23295997, compound

HRID 1954282
Notes
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Reaction equation

HRID 1954282 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9].[CH2:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[CH3:16]>C(Cl)Cl>[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([C:21]1[CH:20]=[CH:19][C:18]([O:23][CH3:24])=[C:17]([CH2:15][CH3:16])[CH:22]=1)=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 691102-Chlorobenzoyl chlorideHCID 84654Benzene, 1-ethyl-2-methoxy-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 23295997HCID 23295997, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At ambient temperature, to a stirred solution containing aluminum chloride (20 g, 0.150 mol), 2-chlorobenzoylchloride (19 mL, 0.150 mol) in CH2Cl2 (100 mL) was added dropwise 2-ethylanisole (20.4 g, 0.150 mol). After 4 h, the reaction was diluted with CH2Cl2 (400 mL) washed with aq. KH2PO4 (2×200 mL), brine (1×200 mL), filtered though Celite and concentrated to give 38.82 g (94%) of the title compound. 1H NMR: consistent.

Workup

  1. washwashed with aq. KH2PO4 (2×200 mL), brine (1×200 mL)
  2. filtrationfiltered though Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-800410df58bb40e49f72d385193df258
Source dataset
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06121271

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes