M-Cresol → NSC406958

HRID 364975Notes

Reaction equation

HRID 364975 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 4-bromoanisole 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 2N hydrochloric acid, three times with 100 ml of 2N 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 2N hydrochloric acid, three times with 100 ml of 2N 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-8d1777b57f184f10ab3c9d1c2b304bc6
Source dataset
uspto-grants-1986_08
Patent number
US04607051

Reaction notes

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