Allyl chloride → Methanone, [4,6-dihydroxy-5-(2-propenyl)-1,3-phenylene]bis[phenyl-

HRID 275084Notes

Reaction equation

HRID 275084 reaction equation
[C:1]([C:9]1[CH:15]=[C:14]([C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([OH:13])=[CH:11][C:10]=1[OH:24])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:27](Cl)[CH:28]=[CH2:29]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:29]([C:11]1[C:12]([OH:13])=[C:14]([C:16](=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:15]=[C:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]=1[OH:24])[CH:28]=[CH2:27]

Participants

5

Reactant 3

HCID 7850Allyl chlorideHCID 14798Sodium HydroxideHCID 5204954,6-Dibenzoylresorcinol

Product 1

HCID 7010346Methanone, [4,6-dihydroxy-5-(2-propenyl)-1,3-phenylene]bis[phenyl-Yield 67%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

A round bottomed flask equipped with a reflux condenser and magnetic stirrer was charged with 6.36 g (20 mmol) of 4,6-dibenzoylresorcinol, as prepared in Example 1, and 22 ml of 1.0N aqueous NaOH. 63 mg of tetrabutylammonium bromide and 10.0 ml of allyl chloride were added to produce a reaction mixture. The reaction mixture was stirred vigorously and heated at reflux for about 5 hours. Excess allyl chloride was distilled and recovered and 1 ml of 5% aqueous HCl was added to neutralize any excess base. The resulting solid was filtered and recrystallized from an ethanol/chloroform mixture to yield 4.8 g (67%) of 2-allyl-4,6-dibenzoylresorcinol.

Workup

  1. customA round bottomed flask equipped with a reflux condenser and magnetic stirrer
  2. customto produce a reaction mixture
  3. temperatureheated
  4. temperatureat reflux for about 5 hours
  5. distillationExcess allyl chloride was distilled
  6. customrecovered
  7. addition1 ml of 5% aqueous HCl was added
  8. filtrationThe resulting solid was filtered
  9. customrecrystallized from an ethanol/chloroform mixture

Sources & evidence

ORD record
ord-74108096ca484981982b0029c9e0f00f
Source dataset
uspto-grants-1995_02
Patent number
US05391795

Reaction notes

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