Triethylamine → 2-Octyl-1-benzofuran

HRID 3061Notes

Reaction equation

HRID 3061 reaction equation
[Br-].OC1C=CC=CC=1C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:29]([O:39][C:40](=O)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])(=O)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]CC.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:41]([C:40]1[O:39][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=2[CH:35]=1)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74304Nonan-1-oic anhydrideHCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromide

Product 1

HCID 37871882-Octyl-1-benzofuranYield 76.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

112 g (249 mM) of (2-hydroxybenzyl)triphenylphosphonium bromide, 83 g (278 mM) of nonanoic anhydride, 104 g (1.03 mM) of triethylamine and 800 ml of toluene were placed in a 3 1-three-necked flask, followed by refluxing for 4.5 hours under stirring. After the reaction, the reaction mixture was left standing at room temperature to precipitate a crystal. The crystal was removed by filtration. The filtrate was concentrated and purified by silica gel column chromatography (eluent:toluene/hexane=1/1) to obtain 44 g of liquid 2-octylbenzofuran (Yield: 76.6%).

Workup

  1. temperatureby refluxing for 4.5 hours
  2. customAfter the reaction
  3. waitthe reaction mixture was left
  4. customstanding at room temperature
  5. customto precipitate a crystal
  6. customThe crystal was removed by filtration
  7. concentrationThe filtrate was concentrated
  8. custompurified by silica gel column chromatography (eluent:toluene/hexane=1/1)

Sources & evidence

ORD record
ord-7cfb9a4aa79d4897a5745b991d796205
Source dataset
uspto-grants-1998_03
Patent number
US05733476

Reaction notes

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