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

HRID 2050088Notes

Reaction equation

HRID 2050088 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, dilute 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, dilute 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-db7261bb0919436a9fe4ad734e5c6cfb
Source dataset
uspto-grants-1980_04
Patent number
US04199595

Reaction notes

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