Water → HCID 23338848, compound

HRID 28094Notes

Reaction equation

HRID 28094 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH:7]2[CH:9]([C:10]([OH:12])=[O:11])[C:8]2([CH3:14])[CH3:13])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]O)=[CH:24][C:23]=1[O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O>CN(C=O)C.C1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH:9]([C:10]([O:12][CH2:26][C:25]3[CH:28]=[CH:29][C:22]([F:21])=[C:23]([O:30][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:24]=3)=[O:11])[C:8]2([CH3:13])[CH3:14])=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 12874224(4-Fluoro-3-phenoxyphenyl)methanolHCID 203049613-(4-Chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid

Product 1

HCID 23338848HCID 23338848, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid (0.95 g, 3.95 mmol), thionyl chloride (0.342 ml, 4.74 mmol) and DMF (several drops) in 50 ml benzene is stirred at RT for 2 days. The solvent and excess thionyl chloride are evaporated under reduced pressure. The resulting acid chloride is dissolved in 50 ml benzene, and 0.86 g 4-fluoro-3-phenoxybenzyl alcohol (3.95 mmol) and 0.482 g 4-dimethylaminopyridine (3.95 mmol) are added. The mixture is left at 25° for 18 hours and then heated under reflux for 2 hours. The mixture is then poured into water and extracted with ether. The organic phase is washed with dilute HCl, sat. NaHCO3, water and brine, dried and concentrated under vacuum. The crude product is purified by preparative TLC developing with 20% ethyl acetate/hexane to yield 4-fluoro-3-phenoxybenzyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate.

Workup

  1. customThe solvent and excess thionyl chloride are evaporated under reduced pressure
  2. dissolutionThe resulting acid chloride is dissolved in 50 ml benzene
  3. waitThe mixture is left at 25° for 18 hours
  4. temperatureheated
  5. temperatureunder reflux for 2 hours
  6. extractionextracted with ether
  7. washThe organic phase is washed with dilute HCl, sat. NaHCO3, water and brine
  8. customdried
  9. concentrationconcentrated under vacuum
  10. customThe crude product is purified by preparative TLC

Sources & evidence

ORD record
ord-021fed2a9abf4a7d94591fca4bba9227
Source dataset
uspto-grants-1980_09
Patent number
US04225533

Reaction notes

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