Hydrochloric Acid → HCID 54515227, compound

HRID 1995679

Reaction equation

HRID 1995679 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.[CH:17]1([CH:20]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[C:21](Cl)=[O:22])[CH2:19][CH2:18]1.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:21](=[O:22])[CH:20]([C:24]1[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=1)[CH:17]1[CH2:19][CH2:18]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 15083505alpha-Cyclopropyl-4-chlorophenylacetyl chloride

Product 1

HCID 54515227HCID 54515227, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

9.4 g (0.043 mol) of 3-phenoxy-4-fluoro-benzyl alcohol and 9.9 g (0.043 mol) of α-cyclopropyl-4-chlorophenyl-acetic acid chloride were dissolved in 100 ml of anhydrous toluene, and 4 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° C. for a further 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 waterpump vacuum. Last residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 14.9 g (84.4% of theory) of α-cyclopropyl-4-chlorophenyl-acetic acid 3-phenoxy-4-fluoro-benzyl ester were obtained as a yellow oil. The structure was confirmed by the H--NMR spectrum.

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-6843bd4ff5a940648d50483e38644740
Source dataset
uspto-grants-1983_09
Patent number
US04405639

Linked notes

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