Benzyltrimethylammonium hydroxide → 2-Methylpentane

HRID 2234199Notes

Reaction equation

HRID 2234199 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][OH:13].[OH-:14].[CH2:15]([N+](C)(C)C)[C:16]1[CH:21]=CC=C[CH:17]=1>CO>[CH3:9][CH2:10][CH2:1][CH:2]([CH3:11])[CH3:3].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][O:13][CH2:2][CH2:11][C:12]([O:13][C:16]([CH3:15])([CH3:17])[CH3:21])=[O:14]

Participants

5

Reactant 2

HCID 66854Benzyltrimethylammonium hydroxideHCID 738772-Naphthaleneethanol

Product 2

HCID 78922-MethylpentaneHCID 86258460HCID 86258460, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

2-Naphthalene ethanol (3 g) was treated with benzyltrimethylammonium hydroxide (Triton B®; 198 uL of a 40% solution in methanol). The methanol was removed by evaporation and residue azeotroped with toluene (×2). THF (5 ml) was added. The mixture was cooled to 0° C. and tert Butyl acrylate (2.45 g) added slowly. The mixture was stirred for 4 days. The majority of the THF was removed by evaporation, and the residue purified using silica column chromatography, eluting with isohexane, then 2:1 isohexane:ethyl acetate to give the sub-titled compound (4.96 g).

Workup

  1. customThe methanol was removed by evaporation and residue
  2. customazeotroped with toluene (×2)
  3. additionTHF (5 ml) was added
  4. additiontert Butyl acrylate (2.45 g) added slowly
  5. customThe majority of the THF was removed by evaporation
  6. customthe residue purified
  7. washeluting with isohexane

Sources & evidence

ORD record
ord-6d29844158334b469f4f22f69621a602
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

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