Aluminum(III) Chloride → 3-(4-Hydroxy-3,5-di-methoxy-benzoyl)-7-hydroxy-6-methoxy-2-Methyl-benzo[b]furan

HRID 529268Notes

Reaction equation

HRID 529268 reaction equation
[CH3:1][C:2]1[O:6][C:5]2[C:7]([OH:13])=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:4]=2[C:3]=1[C:14](=[O:27])[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23]C)=[C:17]([O:25][CH3:26])[CH:16]=1.[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[OH:23][C:18]1[C:19]([O:21][CH3:22])=[CH:20][C:15]([C:14]([C:3]2[C:4]3[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([OH:13])[C:5]=3[O:6][C:2]=2[CH3:1])=[O:27])=[CH:16][C:17]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) Chloride2×HCID 24786555Bnc-105

Product 1

HCID 248803213-(4-Hydroxy-3,5-di-methoxy-benzoyl)-7-hydroxy-6-methoxy-2-Methyl-benzo[b]furan

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl-3-(3,4,5-trimethoxybenzoyl)-7-hydroxy-6-methoxy-benzo[b]furan Example 11 (100 mg, 0.27 mmol) was dissolved in dry dichloromethane (5 mL) and solid aluminium trichloride (72 mg, 0.54 mmol) was added to it. The mixture was stirred for 2 hours when additional amount of aluminium trichloride (72 mg, 0.54 mmol) was added and the stirring was continued for 2 more hours (tlc). The reaction was quenched with saturated solution of ammonium chloride and diluted with DCM (20 mL) the organic layer was separated and washed with water, dried over magnesium sulphate and solvent was distilled to gave the crude product which was purified over silica gel column. The compound was crystallized from methanol to gave the product as white solid. (42 mg, 44%). 1H NMR (300 MHz, CDCl3) δ 7.16 (s, 2H, benzoyl Hs), 6.91 (d, J=8.58 Hz, 1H), 6.83 (d, J=8.58 Hz, 1H), 5.94 (s, 1H, OH), 5.68 (s, 1H, OH), 3.91 (s, 3H, OMe), 3.87 (s, 6H, 2×OMe), 2.54 (s, 3H, Me).

Workup

  1. additionwas added
  2. customThe reaction was quenched with saturated solution of ammonium chloride
  3. additiondiluted with DCM (20 mL) the organic layer
  4. customwas separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate and solvent
  7. distillationwas distilled
  8. customto gave the crude product which
  9. customwas purified over silica gel column
  10. customThe compound was crystallized from methanol

Sources & evidence

ORD record
ord-beb4e4a8f4a74045affd8f62da072b1b
Source dataset
uspto-grants-2016_05
Patent number
US09346842B2

Reaction notes

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