Sodium Hydroxide → 1H-Indole, 2,3-dihydro-3,3-dimethyl-2-methylene-1-octadecyl-

HRID 1957082Notes

Reaction equation

HRID 1957082 reaction equation
[CH3:1][CH:2]1[C:10]([CH3:12])([CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[Br-].[CH2:14]([NH3+])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].[OH-].[Na+]>O>[CH3:12][C:10]1([CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])[C:2]1=[CH2:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 109427602,3,3-TRIMETHYLINDOLINEHCID 21932949HCID 21932949, compound

Product 1

HCID 110801231H-Indole, 2,3-dihydro-3,3-dimethyl-2-methylene-1-octadecyl-Yield 84.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.2 g (32 mmol) of 2,3,3-trimethylindoline and 15.8 g (48 mmol) of octadecylammonium bromide was heated with stirring followed by treating with a solution of 8 g of sodium hydroxide in 50 ml of water. After usual working-up, there were obtained 4.2 g of the title compound in a 84.1% yield.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-cfd9262709cd4727a6d4a6aa9eb72577
Source dataset
uspto-grants-1998_07
Patent number
US05782969

Reaction notes

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