Dichloromethane → HCID 11417330, compound

HRID 896845Notes

Reaction equation

HRID 896845 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=O.ClCCl.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH3:28])[CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C(OC)(C)(C)C.CCCCCC.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([CH3:12])[C:3]=1[C:4]([C:21]1[C:22]([O:26][CH3:27])=[C:23]([O:24][CH3:25])[C:18]([O:17][CH3:16])=[CH:19][C:20]=1[CH3:28])=[O:6]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14812Phosphorus oxide (P4O10)HCID 809223,4,5-TrimethoxytolueneHCID 111950733,6-Dichloro-2-methylbenzoic acid

Product 1

HCID 11417330HCID 11417330, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21982663Methyl t-butylether hexaneSolvent

Procedure

14 g (68.29 mmol) of 2,5-dichloro-6-methylbenzoic acid were introduced into 1000 ml of dichloromethane. 11.2 g (61.6 mmol) of 3,4,5-trimethoxytoluene and 28 g of finely ground phosphorus pentoxide were added. After 2 hours of stirring at room temperature, the reaction solution, which by now was orangey red, was poured into water and extracted three times with dichloromethane. The combined organic phases were washed twice with water, dried with sodium sulfate and concentrated, and the reaction product was then isolated by column chromatography using a methyl tert-butyl ether/hexane gradient. This gave 20.1 g of the title compound (yield 80%).

Workup

  1. extractionextracted three times with dichloromethane
  2. washThe combined organic phases were washed twice with water
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customthe reaction product was then isolated by column chromatography

Sources & evidence

ORD record
ord-ea9a12b0c1e54f7fb59341ba4c6d11ac
Source dataset
uspto-grants-2005_07
Patent number
US06919485B2

Reaction notes

Loading…