3-Pyridinemethanol → 3-Pyridylmethyl (3-Trifluoromethylphenoxy)(4-chlorophenyl)acetate hydrochloride

HRID 973187Notes

Reaction equation

HRID 973187 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.C(N(CC)CC)C.[F:16][C:17]([F:37])([F:36])[C:18]1[CH:19]=[C:20]([CH:33]=[CH:34][CH:35]=1)[O:21][CH:22]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:23]([Cl:25])=[O:24]>CCOCC>[ClH:25].[F:36][C:17]([F:16])([F:37])[C:18]1[CH:19]=[C:20]([CH:33]=[CH:34][CH:35]=1)[O:21][CH:22]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:23]([O:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[O:24]

Participants

5

Reactant 3

HCID 75103-PyridinemethanolHCID 8471TriethylamineHCID 121092354-Chloro-α-[3-(trifluoromethyl)phenoxy]benzeneacetyl chloride

Product 1

HCID 1317109433-Pyridylmethyl (3-Trifluoromethylphenoxy)(4-chlorophenyl)acetate hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 3-pyridylcarbinol (5.7 g., 0.0522 mole) in triethylamine (144 ml., 0.13 mole) is cooled to -15° C. To this solution is added (3-trifluoromethylphenoxy)(4-chlorophenyl)acetyl chloride (18 g., 0.0515 mole) in ether (25 ml.). The reaction mixture is stirred for four hours at -5° C. and then at room temperature for 4 hours. The reaction mixture is filtered and the filtrate is washed successively with water, dilute sodium bicarbonate and then water until neutral. The ether solution is dried over magnesium sulfate filtered and to this solution is added ethanolic HCl. An oil separated which slowly crystallized. The solid is collected and recrystallized from a mixture of of isopropanol (30 ml.) and ether (30 ml.) to afford 8.6 g. of product. A small sample recrystallized for analysis has a melting point of 147°-149° C.

Workup

  1. waitat room temperature for 4 hours
  2. filtrationThe reaction mixture is filtered
  3. washthe filtrate is washed successively with water, dilute sodium bicarbonate
  4. dry with materialThe ether solution is dried over magnesium sulfate
  5. filtrationfiltered and to this solution
  6. additionis added ethanolic HCl
  7. customAn oil separated which
  8. customslowly crystallized
  9. customThe solid is collected
  10. customrecrystallized from a mixture of of isopropanol (30 ml.) and ether (30 ml.)
  11. customto afford 8.6 g
  12. customA small sample recrystallized for analysis

Sources & evidence

ORD record
ord-1dd81f895c624ab39efc8dd199e78df4
Source dataset
uspto-grants-1977_10
Patent number
US04055592

Reaction notes

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