Hydrochloric Acid → HCID 54160409, compound

HRID 851326Notes

Reaction equation

HRID 851326 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]1([CH3:35])[CH:20]([CH:21]=[C:22]([Cl:31])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[CH:19]1[C:32](Cl)=[O:33].N1C=CC=CC=1.Cl>C1(C)C=CC=CC=1.O>[F:16][C:15]1[CH:14]=[CH:13][C:10]([CH2:11][O:12][C:32]([CH:19]2[CH:20]([CH:21]=[C:22]([Cl:31])[C:23]3[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)[C:18]2([CH3:35])[CH3:17])=[O:33])=[CH:9][C:8]=1[O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 12874224(4-Fluoro-3-phenoxyphenyl)methanolHCID 53893220HCID 53893220, compound

Product 1

HCID 54160409HCID 54160409, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

4.4 g (0.02 mol) of 3-phenoxy-4-fluoro-benzyl alcohol and 7.1 g (0.02 mol) of 2,2-dimethyl-3-(2-chloro-2-(4-methoxy-phenyl)-vinyl)-cyclopropanecarboxylic acid chloride were dissolved in 100 ml of anhydrous toluene, and 2.5 g of pyridine, dissolved in 50 ml of anhydrous toluene, were added dropwise at 20°-25° C., whilst stirring. Stirring was then continued at 25°-35° C. for 3 hours. The reaction mixture was poured into 150 ml of water, to which 10 ml of concentrated hydrochloric acid were added, and the organic phase was separated off and washed again with 100 ml of water. The toluene phase was then dried over sodium sulphate and the solvent was distilled off under a waterpump vacuum. Last solvent residues were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 8.1 g (84.5% of theory) of 2,2-dimethyl-3-(2-chloro-2-(4-methoxy-phenyl)-vinyl)-cyclopropanecarboxylic acid 4-fluoro-3-phenoxy-benzyl ester were obtained.

Workup

  1. additionwere added dropwise at 20°-25° C.
  2. stirringStirring
  3. additionwere added
  4. customthe organic phase was separated off
  5. washwashed again with 100 ml of water
  6. dry with materialThe toluene phase was then dried over sodium sulphate
  7. distillationthe solvent was distilled off under a waterpump vacuum
  8. customLast solvent residues were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg

Sources & evidence

ORD record
ord-db7603dcfe25494ca5ad42480af6853e
Source dataset
uspto-grants-1983_05
Patent number
US04384114

Reaction notes

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