Hydrochloric Acid → HCID 53700099, compound

HRID 1447441Notes

Reaction equation

HRID 1447441 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([CH3:38])[CH:20]([CH:21]=[C:22]([Cl:34])[C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=2)[CH:19]1[C:35](Cl)=[O:36].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:35]([CH:19]2[CH:20]([CH:21]=[C:22]([Cl:34])[C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:31])[F:32])=[CH:25][CH:24]=3)[C:18]2([CH3:38])[CH3:17])=[O:36])=[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 53824254HCID 53824254, compound

Product 1

HCID 53700099HCID 53700099, compoundYield 81.4%

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-trifluoromethoxy-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., while 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 water-pump vacuum. Last residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 8.7 g (81.4% of theory) of 2,2-dimethyl-3-(2-chloro-2-(4 -trifluoromethoxy-phenyl)-vinyl)-cyclopropanecarboxylic acid 4-fluoro-3-phenoxy-benzyl ester were obtained as a yellow oil with the refractive index nD23 : 1.5443.

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 water-pump 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-79a914820d9047aca5d46d67714f1df0
Source dataset
uspto-grants-1982_02
Patent number
US04316913

Reaction notes

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