M-Cresol → NSC406958

HRID 1732161Notes

Reaction equation

HRID 1732161 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.[Cu]Cl>[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

6

Reactant 3

HCID 342M-CresolHCID 77304-BromoanisoleHCID 24758Sodium hydride

Product 1

HCID 347990NSC406958

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 1049PyridineSolvent3×

Conditions

Temperature
170 °C

Procedure

21.8 g of sodium hydride (55% in oil) are introduced into 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 copper (I) chloride are added and subsequently 93.5 g of 4-bromoanisole are added dropwise at reflux temperature during 1 hour. After heating at reflux for 4 hours the pyridine is distilled off, whereby at the end the mixture is warmed to 170° C. (internal temperature). After 2 hours 350 ml of water are added dropwise while cooling with ice, followed by 500 ml of diethyl ether and an additional 150 ml of water. The mixture is suction filtered 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 anhydrous sodium sulfate and evaporation there is obtained a brown-red oil which is firstly 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 during 1 hour
  3. temperatureAfter heating
  4. distillationis distilled off
  5. additionAfter 2 hours 350 ml of water are added dropwise
  6. temperaturewhile cooling with ice
  7. filtrationfiltered 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 anhydrous sodium sulfate
  11. customevaporation there
  12. customis obtained a brown-red oil which
  13. filtrationis firstly filtered over a five-fold amount of silica gel with n-hexane/diethyl ether
  14. distillationdistilled

Sources & evidence

ORD record
ord-d48568eff487407fb04bf5fe62a131e7
Source dataset
uspto-grants-1986_11
Patent number
US04625048

Reaction notes

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