Hydrochloric Acid → HCID 54304438, compound

HRID 848763Notes

Reaction equation

HRID 848763 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][C:17]1([CH3:32])[CH:19]([CH:20]=[C:21]([O:26][CH2:27][CH3:28])[C:22]([F:25])([F:24])[F:23])[CH:18]1[C:29](Cl)=[O:30].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][CH:15]=1)[CH2:11][O:12][C:29]([CH:18]1[CH:19]([CH:20]=[C:21]([O:26][CH2:27][CH3:28])[C:22]([F:25])([F:23])[F:24])[C:17]1([CH3:16])[CH3:32])=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 262953-Phenoxybenzyl alcoholHCID 53757527HCID 53757527, compound

Product 1

HCID 54304438HCID 54304438, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

5.2 g (0.026 mol) of 3-phenoxy-benzyl alcohol and 7 g (0.026 mol) of 2,2-dimethyl-3-(3,3,3-trifluoro-2-ethoxy-prop-1-enyl)-cyclopropanecarboxylic acid chloride were dissolved in 100 ml of anhydrous toluene, and 2.5 g of pyridine, dissolved in 20 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. 9.9 g (87.7% of theory) of 2,2-dimethyl-3-(3,3,3-trifluoro-2-ethoxy-prop-1-enyl)-cyclopropanecarboxylic acid 3-phenoxybenzyl ester were obtained as a yellow oil with the refractive index nD25 : 1.5130.

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-c62a85f66e1a4912a0bd4ee30450ff53
Source dataset
uspto-grants-1981_10
Patent number
US04297366

Reaction notes

Loading…