Hydrochloric Acid → HCID 13041082, compound

HRID 2199002Notes

Reaction equation

HRID 2199002 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:15](Cl)=[O:16])[CH2:12][C:11]2([Cl:14])[Cl:13])=[CH:6][CH:5]=1)[CH3:2].[O:18]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[F:33])[CH2:28][OH:29])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.N1C=CC=CC=1.Cl>C1(C)C=CC=CC=1.O>[O:18]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[F:33])[CH2:28][O:29][C:15]([C:10]1([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)[CH2:12][C:11]1([Cl:14])[Cl:13])=[O:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 12874224(4-Fluoro-3-phenoxyphenyl)methanolHCID 130410812,2-Dichloro-1-(4-ethoxyphenyl)cyclopropane-1-carbonyl chloride

Product 1

HCID 13041082HCID 13041082, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

5.87 g (0.02 mole) of (±)-1-(4-ethoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid chloride and 4.36 g (0.02 mole) of 3-phenoxy-4-fluoro-benzyl alcohol were dissolved in 100 ml of anhydrous toluene, and 3 g of pyridine, dissolved in 50 ml of anhydrous toluene, were added dropwise at 20° to 25° C., while stirring. The reaction mixture was then stirred at 25° C. for a further 3 hours. It 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 residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 8.1 g (85.3% of theory) of (±)-1-(4-ethoxy-phenyl)-2,2-dichlorocyclopropane- 1-carboxylic acid 3-phenoxy-4-fluorobenzyl ester were obtained as a yellow oil. The structure was confirmed by the 1H-NMR spectrum.

Workup

  1. additionwere added dropwise at 20° to 25° C.
  2. stirringThe reaction mixture was then stirred at 25° C. for a further 3 hours
  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 residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg

Sources & evidence

ORD record
ord-5febce2fb1de4102addea36e01b58604
Source dataset
uspto-grants-1982_11
Patent number
US04360690

Reaction notes

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