Sodium Iodide → HCID 21545459, compound

HRID 1605863Notes

Reaction equation

HRID 1605863 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH:8](Br)[CH2:9][CH2:10][Cl:11])=[O:7])=[CH:4][CH:3]=1.[C:15]1([OH:25])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.[I-].[Na+].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH:8]([O:25][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[CH2:9][CH2:10][Cl:11])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 70051-NaphtholHCID 11430Potassium CarbonateHCID 30165872-Bromo-4-chloro-1-(4-fluorophenyl)butan-1-one

Product 1

HCID 21545459HCID 21545459, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

The 1-p-Fluorobenzoyl-1-(alpha-naphthoxy)-3-chloropropane is prepared as follows. A solution of 20 g. of 1-p-fluorobenzoyl-1-bromo-3-chloropropane in 60 cc. anhydrous acetone is added slowly over half an hour while stirring to a suspension of 10.4 g. of α-naphthol, 0.72 g. of sodium iodide and 16.8 g. of K2CO3 in 300 cc. anhydrous acetone. When the addition is complete, the mixture is refluxed for 10 hours and then cooled. The solid therein is filtered off and the solvent is removed from the filtrate at reduced pressure. The residue melts at 147°C (from benzene).

Workup

  1. additionWhen the addition
  2. temperaturethe mixture is refluxed for 10 hours
  3. temperaturecooled
  4. filtrationThe solid therein is filtered off
  5. customthe solvent is removed from the filtrate at reduced pressure

Sources & evidence

ORD record
ord-a7c171f92a334b27b809e790f0529dc0
Source dataset
uspto-grants-1976_04
Patent number
US03951978

Reaction notes

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