Dichloromethane → HCID 10949234, compound

HRID 1066283Notes

Reaction equation

HRID 1066283 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([C:8]([CH3:11])=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH3:25])[CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.ClCCl>O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:4]([C:3]=1[CH3:12])[C:5]([C:16]1[C:17]([CH3:25])=[CH:18][C:19]([O:23][CH3:24])=[C:20]([O:21][CH3:22])[C:15]=1[O:14][CH3:13])=[O:7]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14812Phosphorus oxide (P4O10)HCID 809223,4,5-TrimethoxytolueneHCID 81671423-bromo-2,6-dimethylbenzoic acid

Product 1

HCID 10949234HCID 10949234, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1B (1.3 g, 5.7 mmol), 3,4,5-trimethoxytoluene (1.0 g; 5.7 mmol), P2O5 (3.5 g) and dichloromethane (20 ml) is stirred at room temperature for 16 hours. Subsequently, water (5 ml) and ice are added and dichloromethane is distilled off and the residue is extracted with toluene. The organic phase is washed with water and concentrated. The residue is recrystallized from petrol ethers/toluene. The solid material is collected by vacuum filtration, washed with cold petrol ethers and dried, yielding white crystals, 1.4 g, mp 859° C.

Workup

  1. distillationdichloromethane is distilled off
  2. extractionthe residue is extracted with toluene
  3. washThe organic phase is washed with water
  4. concentrationconcentrated
  5. customThe residue is recrystallized from petrol ethers/toluene
  6. filtrationThe solid material is collected by vacuum filtration
  7. washwashed with cold petrol ethers
  8. customdried
  9. customyielding white crystals, 1.4 g, mp 859° C.

Sources & evidence

ORD record
ord-9e04bfd472c9428a8a73f6056b1dd217
Source dataset
uspto-grants-2001_06
Patent number
US06242498B1

Reaction notes

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