Hydrochloric Acid → 2,2,3,3-Tetramethyl-cyclopropanecarboxylic acid 3-(4-fluorophenoxy)-benzyl ester

HRID 2058669Notes

Reaction equation

HRID 2058669 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH2:10][OH:11])=[CH:4][CH:3]=1.[CH3:17][C:18]1([CH3:26])[C:20]([CH3:22])([CH3:21])[CH:19]1[C:23](Cl)=[O:24].N1C=CC=CC=1.Cl>C1(C)C=CC=CC=1.O>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH2:10][O:11][C:23]([CH:19]2[C:20]([CH3:22])([CH3:21])[C:18]2([CH3:26])[CH3:17])=[O:24])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10584901[3-(4-Fluorophenoxy)phenyl]methanolHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chloride

Product 1

HCID 128843492,2,3,3-Tetramethyl-cyclopropanecarboxylic acid 3-(4-fluorophenoxy)-benzyl esterYield 81.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

5.05 g (0.0232 mol) of 3-(4-fluoro-phenoxy)-benzyl alcohol and 3.72 g (0.0232 mol) of 2,2,3,3-tetramethylcyclopropanecarboxylic acid chloride were dissolved in 100 ml of anhydrous toluene, and 2.3 g of pyridine, dissolved in 50 ml of anhydrous toluene, were added dropwise at 20°-25° C., while stirring. The reaction mixture was then stirred for a further 3 hours at 25° C. It was poured into 150 ml of water, to which 10 ml of concentrated hydrochloric acid had been 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. 6.5 g (81.9% of theory) of 2,2,3,3-tetramethyl-cyclopropanecarboxylic acid 3-(4-fluorophenoxy)-benzyl ester were obtained as a yellow oil with a refractive index nD20 of 1.5348.

Workup

  1. additionwere added dropwise at 20°-25° C.
  2. stirringThe reaction mixture was then stirred for a further 3 hours at 25° C
  3. additionhad been 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-a1ad5e5b8c524e6893b300051c584a3c
Source dataset
uspto-grants-1982_03
Patent number
US04318922

Reaction notes

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