M-Cresol → NSC406958

HRID 1648776Notes

Reaction equation

HRID 1648776 reaction equation
[H-].[Na+].[CH:3]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:10].Br[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[C:4]1([CH3:10])[CH:5]=[CH:6][CH:7]=[C:8]([O:9][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 342M-CresolHCID 77304-BromoanisoleHCID 24758Sodium hydride

Product 1

HCID 347990NSC406958

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
170 °C

Procedure

21.8 g of sodium hydride (55% in oil) are placed in 100 ml of absolute pyridine and treated dropwise during 1 hour with 54.1 g of m-cresol in 200 ml of pyridine. After completion of the reaction, 1.2 g of cuprous chloride are added and subsequently 93.5 g of 4bromoanisole are added dropwise during 1 hour at reflux temperature. After refluxing for 4 hours, the pyridine is distilled off, the mixture being heated at the end up to 170° C. (internal temperature). After 2 hours, 350 ml of water are added dropwise with ice-cooling, followed by 500 ml of diethyl ether and a further 150 ml of water. The mixture is filtered with suction over Celite and the phases are separated. The organic phase is washed in sequence with 200 ml of 2 N hydrochloric acid, three times with 100 ml of 2 N sodium hydroxide each time, with 200 ml of water and with 200 ml of saturated sodium chloride solution. After drying over sodium sulfate and evaporation, there is obtained a brown-red oil which is filtered over a five-fold amount of silica gel with n-hexane/diethyl ether and then distilled to yield pure p-(m-tolyloxy)anisole; b.p. 106°-108° C./0.04 Torr; nD20 =1.5738.

Workup

  1. additionare added
  2. temperatureat reflux temperature
  3. temperatureAfter refluxing for 4 hours
  4. distillationthe pyridine is distilled off
  5. addition350 ml of water are added dropwise with ice-
  6. temperaturecooling
  7. filtrationThe mixture is filtered with suction over Celite
  8. customthe phases are separated
  9. washThe organic phase is washed in sequence with 200 ml of 2 N hydrochloric acid, three times with 100 ml of 2 N sodium hydroxide each time
  10. dry with materialAfter drying over sodium sulfate and evaporation
  11. customthere is obtained a brown-red oil which
  12. filtrationis filtered over a five-fold amount of silica gel with n-hexane/diethyl ether
  13. distillationdistilled

Sources & evidence

ORD record
ord-969e77e12c4e436db966241d00f1ba71
Source dataset
uspto-grants-1983_11
Patent number
US04413010

Reaction notes

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