Pyridine → m-Phenoxybenzyl alpha-isopropyl-4-trifluoromethoxyphenylacetate

HRID 1447921Notes

Reaction equation

HRID 1447921 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.N1C=CC=CC=1.[CH:22]([CH:25]([C:29]1[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=1)[C:26](Cl)=[O:27])([CH3:24])[CH3:23]>C(Cl)Cl>[CH:22]([CH:25]([C:29]1[CH:34]=[CH:33][C:32]([O:35][C:36]([F:37])([F:38])[F:39])=[CH:31][CH:30]=1)[C:26]([O:12][CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1)=[O:27])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 262953-Phenoxybenzyl alcoholHCID 20343288HCID 20343288, compound

Product 1

HCID 20343285m-Phenoxybenzyl alpha-isopropyl-4-trifluoromethoxyphenylacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of m-phenoxybenzyl alcohol (1.89 g) and pyridine (1 ml) in methylene chloride (6 ml) is added a methylene chloride (7 ml) solution of α-isopropyl-4-trifluoromethoxyphenylacetyl chloride, prepared from the corresponding acid (2.46 g) as illustrated in Example 15. After stirring the reaction mixture overnight, it is washed with water, diluted hydrochloric acid solution, dilute potassium hydroxide solution, water and evaporated to an orange oil. Purification by silica gel chromatography gives the desired ester (2.76 g).

Workup

  1. washis washed with water, diluted hydrochloric acid solution, dilute potassium hydroxide solution, water
  2. customevaporated to an orange oil
  3. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-22765441f38e4e9d888cbf327b4ab857
Source dataset
uspto-grants-1979_12
Patent number
US04178460

Reaction notes

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