Water → HCID 18672472, compound

HRID 2288893Notes

Reaction equation

HRID 2288893 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[OH:24])[CH2:16][CH3:17].O>ClCCCl.C(Cl)Cl>[OH:24][C:19]1[C:18]([CH2:15][CH2:16][CH3:17])=[CH:23][C:22]([C:4]([C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[F:1])=[O:5])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 98082-Fluorobenzoyl chlorideHCID 125702-PropylphenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18672472HCID 18672472, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A 0° C. suspension of 2-fluorobenzoyl chloride (1.3 mL, 11.03 mmol) in 15 mL of 1,2-dichloroethane was treated with aluminum chloride (1.0 g, 7.35 mmol). The suspension was vigorously stirred for 15 minutes. A solution of 2-propylphenol (1.0 g, 7.35 mmol) in 5 mL of 1,2-dichloro-ethane was added dropwise. The mixture was allowed to stir and gradually warm to 25° C. over 6 hours. The mixture was slowly added to a stirred mixture of water and methylene chloride. The organic phase was dried over magnesium sulfate, filtered and concentrated to a solid. The crude residue was purified via flash chromatography on silica gel (15% ethyl acetate/hexane eluent) to afforded the title compound.

Workup

  1. stirringto stir
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a solid
  5. customThe crude residue was purified via flash chromatography on silica gel (15% ethyl acetate/hexane eluent)

Sources & evidence

ORD record
ord-874ab8aac06e41eebf77483d175f1b2e
Source dataset
uspto-grants-2000_07
Patent number
US06090839

Reaction notes

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