Dichloromethane → 5-Chloro-2-(4-methoxy-phenoxy)-benzaldehyde

HRID 504522Notes

Reaction equation

HRID 504522 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[Cl:16][C:17]1[CH:18]=[CH:19][C:20](F)=[C:21]([CH:24]=1)[CH:22]=[O:23].C(Cl)Cl>CN(C)C(=O)C.O>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([O:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)=[C:21]([CH:24]=1)[CH:22]=[O:23]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 90154-MethoxyphenolHCID 10340Sodium CarbonateHCID 27735865-Chloro-2-fluorobenzaldehyde

Product 1

HCID 577501175-Chloro-2-(4-methoxy-phenoxy)-benzaldehydeYield 60.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

At the room temperature, anhydrous Na2CO3 (16 g, 0.15 mol) was added into a mixture of 4-methoxy-phenol (14.8 g, 0.12 mol) and 5-chloro-2-fluoro-benzaldehyde (16 g, 0.10 mol) in N,N-Dimethylacetamide (100 mL). After the mixture was refluxed for 3 h, it was cooled to room temperature. Then DCM and water were added. The organic phase was separated, washed with aqueous NaOH (1 N) and brine, dried over anhydrous Na2SO4 and concentrated to give the title compound (16 g).

Workup

  1. temperatureAfter the mixture was refluxed for 3 h
  2. customThe organic phase was separated
  3. washwashed with aqueous NaOH (1 N) and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7a7dd403969f4058a2dd6a2d4c8f1bf7
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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