Phosphorus oxide (P4O10) → 1-(6'-Methyl-2',3',4'-trimethoxybenzoyl)-2-methoxynaphthalene

HRID 611712

Reaction equation

HRID 611712 reaction equation
CO[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[O:15][CH3:16])=[O:4].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH3:29])[CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>ClCCl>[CH3:29][C:21]1[C:22]([C:3]([C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][C:6]=2[O:15][CH3:16])=[O:4])=[C:23]([O:27][CH3:28])[C:24]([O:25][CH3:26])=[C:19]([O:18][CH3:17])[CH:20]=1

Participants

5

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 809223,4,5-TrimethoxytolueneHCID 604022Methyl 2-methoxy-1-naphthoate

Product 1

HCID 158708981-(6'-Methyl-2',3',4'-trimethoxybenzoyl)-2-methoxynaphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5B (2.02 g, 10 mmol), 3,4,5-trimethoxytoluene (1.82 g; 10 mmol), P2O5 (10.0 g) and dichloromethane 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 ethers:ethyl acetate, 8:2 v/v) and recrystallized from petrol ether:diisopropylether (1:1 v/v). The solid material is collected by vacuum filtration, washed with cold petrol ether:diisopropylether (1:1 v/v) and dried, yielding white crystals, 0.9 g, (24.6%) mp 72° 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 ethers:ethyl acetate, 8:2 v/v)
  6. customrecrystallized from petrol ether:diisopropylether (1:1 v/v)
  7. filtrationThe solid material is collected by vacuum filtration
  8. washwashed with cold petrol ether:diisopropylether (1:1 v/v)
  9. customdried
  10. customyielding white crystals, 0.9 g, (24.6%) mp 72° C.

Sources & evidence

ORD record
ord-14eafedcae5a4def8b11fef508cb35a7
Source dataset
uspto-grants-1999_12
Patent number
US06001883

Linked notes

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