Phosphorus oxide (P4O10) → Metrafenone

HRID 1586589Notes

Reaction equation

HRID 1586589 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([C:10]=1[CH3:11])[C:7]([OH:9])=O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH3:26])[CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([C:10]=1[CH3:11])[C:7]([C:17]1[C:18]([CH3:26])=[CH:19][C:20]([O:24][CH3:25])=[C:21]([O:22][CH3:23])[C:16]=1[O:15][CH3:14])=[O:9]

Participants

5

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 809223,4,5-TrimethoxytolueneHCID 27529923-Bromo-6-methoxy-2-methylbenzoic acid

Product 1

HCID 6451057Metrafenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6B (24 g, 10 mmol), 3,4,5-trimethoxytoluene (1.82 g; 10 mmol), P2O5 (10.0 g) and dichloromethane (150 ml) is stirred at room temperature for 16 hours. Subsequently, the dichloromethane is distilled off and the residue is diluted with ethyl acetate. The organic phase is washed with water and concentrated. The residue is purified by column chromatography (petrol ether: ethyl acetate, 8:2 v/v) and recrystallized from diisopropylether. The solid material is collected by vacuum filtration, washed with cold petrol ethers:diisopropylether (1:1 v/v) and dried, yielding white crystals, 2.2 g (54% ), mp 89-91° C.

Workup

  1. distillationSubsequently, the dichloromethane is distilled off
  2. additionthe residue is diluted with ethyl acetate
  3. washThe organic phase is washed with water
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography (petrol ether: ethyl acetate, 8:2 v/v)
  6. customrecrystallized from diisopropylether
  7. filtrationThe solid material is collected by vacuum filtration
  8. washwashed with cold petrol ethers:diisopropylether (1:1 v/v)
  9. customdried
  10. customyielding white crystals, 2.2 g (54% ), mp 89-91° C.

Sources & evidence

ORD record
ord-898b21864d70457c83225e1eb4875f1f
Source dataset
uspto-grants-1999_08
Patent number
US05945567

Reaction notes

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