Piperidine → HCID 15117839, compound

HRID 2107746Notes

Reaction equation

HRID 2107746 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([C:9]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:10])[CH:6]=[C:4]([OH:5])[C:3]=1[OH:17].[O:18]1[C:20]([CH3:25])([CH2:21][CH2:22][CH:23]=[CH2:24])[CH2:19]1.N1CCCCC1>CCOCC>[OH:18][C:20]([CH3:25])([CH2:21][CH2:22][CH:23]=[CH2:24])[CH2:19][O:5][C:4]1[CH:6]=[C:7]([C:9]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:10])[CH:8]=[C:2]([CH3:1])[C:3]=1[OH:17]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 757163-Methyl-5-(1,1,3,3-tetramethylbutyl)pyrocatecholHCID 147403841,2-Epoxy-2-methyl-5-hexene

Product 1

HCID 15117839HCID 15117839, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 10.5 g (44 mmole) of 3-methyl-5-t-octylcatechol, 11 g (90 mmole) of 1,2-epoxy-2-methyl-5-hexene and 0.75 ml of piperidine was heated at 120° C., with stirring, under nitrogen, for 7 days. The reaction mixture was cooled and dissolved in ether (300 ml), and the resulting solution was washed with water, followed by 1N hydrochloric acid, followed by saturated sodium chloride solution. The washed ethereal solution was dried (MgSO4) and evaporated in vacuo, and the residue was purified by column chromatography on silica gel, eluting with chloroform. This afforded a 25% yield of the title compound as an oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washthe resulting solution was washed with water
  3. dry with materialThe washed ethereal solution was dried (MgSO4)
  4. customevaporated in vacuo
  5. customthe residue was purified by column chromatography on silica gel
  6. washeluting with chloroform

Sources & evidence

ORD record
ord-93f9faae348b4ad9975ec0ed4327b0c5
Source dataset
uspto-grants-1990_06
Patent number
US04935442

Reaction notes

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