Hydrochloric Acid → HCID 53662515, compound

HRID 67132Notes

Reaction equation

HRID 67132 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([CH3:34])[CH:20]([CH:21]=[C:22]([CH3:30])[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH:19]1[C:31](Cl)=[O:32].N1C=CC=CC=1.Cl>C1(C)C=CC=CC=1.O>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:11][O:12][C:31]([CH:19]1[CH:20]([CH:21]=[C:22]([CH3:30])[C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)[C:18]1([CH3:34])[CH3:17])=[O:32])[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 544836402,2-Dimethyl-3-(2-methyl-2-(4-chlorophenyl)-vinyl)-cyclopropanecarboxylic acid chloride

Product 1

HCID 53662515HCID 53662515, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

5.4 g (0.025 mol) of 3-phenoxy-4-fluoro-benzyl alcohol and 7 g (0.025 mol) of 2,2-dimethyl-3-(2-methyl-2-(4-chlorophenyl)-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., while stirring. Stirring was then continued at 25°-35° C. for a further 3 hours. The reaction mixture was poured into 150 ml of water, to which 5 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. 8.7 g (74.9% of theory) of 2,2-dimethyl-3-(2-methyl-2-(4-chlorophenyl)-vinyl)-cyclopropane-carboxylic acid 3-phenoxy-4-fluoro-benzyl ester were obtained as a yellow viscous oil with the refractive index nD23 : 1.5735.

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 residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg

Sources & evidence

ORD record
ord-9adbdd87bd5848ae86fccbb6d1f71ebf
Source dataset
uspto-grants-1982_08
Patent number
US04344963

Reaction notes

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