Pyridine → HCID 13246122, compound

HRID 647559Notes

Reaction equation

HRID 647559 reaction equation
[Cl:1][CH:2]([CH:10]=[C:11]([Cl:13])[Cl:12])[C:3]([CH3:9])([CH3:8])[CH2:4][C:5](Cl)=[O:6].[O:14]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][OH:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1C=CC=CC=1>C1C=CC=CC=1.C(OCC)C>[Cl:1][CH:2]([C:3]([CH3:9])([CH3:8])[CH2:4][C:5]([O:25][CH2:24][C:23]1[CH:26]=[CH:27][CH:28]=[C:21]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:22]=1)=[O:6])[CH:10]=[C:11]([Cl:13])[Cl:12]

Participants

6

Reactant 3

HCID 1049PyridineHCID 262953-Phenoxybenzyl alcoholHCID 132461304,6,6-Trichloro-3,3-dimethylhex-5-enoyl chloride

Product 1

HCID 13246122HCID 13246122, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

In 30 g of dry benzene were dissolved 2.6 g of 4,6,6,-trichloro-3,3-dimethyl-5-hexenoyl chloride and 2.0 g of 3-phenoxybenzyl alcohol were added to the solution. This was followed by the dropwise addition of 2.4 g of pyridine and the mixture was stirred at room temperature overnight. The reaction mixture was then diluted with diethyl ether, washed with dilute aqueous hydrogen chloride and water, dried over anhydrous magnesium sulfate and distilled to remove the low-boiling fraction. The residual viscous oil was purified by column chromatography. By the above procedure there were obtained 3.9 g of 3-phenoxybenzyl β-(1,3,3-trichloroallyl)isovalerate (3-phenoxybenzyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoate, Compound [17]) the NMR spectrum and elemental analysis of which are given below [yield: 91%].

Workup

  1. additionwere added to the solution
  2. washwashed with dilute aqueous hydrogen chloride and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled
  5. customto remove the low-boiling fraction
  6. customThe residual viscous oil was purified by column chromatography

Sources & evidence

ORD record
ord-a492cf8c4bb34d66a00a75d08caf8ade
Source dataset
uspto-grants-1983_10
Patent number
US04409238

Reaction notes

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