Benzene → HCID 21411013, compound

HRID 2072216Notes

Reaction equation

HRID 2072216 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Cl)[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[OH:17][CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+].C1C=CC=CC=1>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[O:17][CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 8880AcetylethanolamineHCID 11430Potassium CarbonateHCID 27237731,1'-(Chloromethylene)bis(4-fluorobenzene)

Product 1

HCID 21411013HCID 21411013, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 25.4 g (0.1 mole) of bis(p-fluorophenyl)methyl chloride, 10.3 g (0.1 mole) of N-(2-hydroxyethyl)acetamide (prepared according to F. J. McQuillin et al., J. Chem. Soc. 1955, 2966), 14 g of potassium carbonate and 100 ml of benzene is refluxed for 5 hours. After cooling, the reaction mixture is poured into water. The aqueous layer is extracted with dichloromethane and the combined organic layers are dried over potassium carbonate and concentrated by evaporation of solvent. The residue is crystallised from toluene. N-{2-[Bis(p-fluorophenyl)methoxy]ethyl}acetamide, m.p. 112°-113.5° C., is obtained.

Workup

  1. temperatureis refluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionThe aqueous layer is extracted with dichloromethane
  4. dry with materialthe combined organic layers are dried over potassium carbonate
  5. concentrationconcentrated by evaporation of solvent
  6. customThe residue is crystallised from toluene

Sources & evidence

ORD record
ord-960ee825475f47fca5a303ae0e21606d
Source dataset
uspto-grants-1977_09
Patent number
US04049825

Reaction notes

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