Methane → HCID 21387599, compound

HRID 1833849Notes

Reaction equation

HRID 1833849 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[O:10][C:9]([C:11]([OH:13])=[O:12])=[CH:8][CH:7]=1)=O.[OH-].[K+].O.NN.C>C(O)COCCO.C(=O)(O)[O-].[Na+].O>[CH3:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:6]1[O:10][C:9]([C:11]([OH:13])=[O:12])=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 21387645HCID 21387645, compound

Product 1

HCID 21387599HCID 21387599, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8117Diethylene GlycolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
145 °C

Procedure

5-(2-Methylbenzoyl)-2-furoic acid [prepared as described in (e) above; 96.6 g.] was added to a solution of potassium hydroxide (70 g.) in diethylene glycol (530 ml.) at 100°-110° C. When the solution was complete, hydrazine hydrate (58%; 53 ml.) was added. The mixture was gradually warmed and then maintained under reflux at 145° C. for 7 hours. Evolution of nitrogen was monitored by collecting the gas over water. Evolution of nitrogen did not completely cease. The reaction mixture was cooled, diluted with water (600 ml.) and stirred while acidifying by dropwise addition of concentrated hydrochloric acid to give crude 5-(2- methylbenzyl)-2-furoic acid in the form of a sticky, brown coloured solid, which was collected, washed with water and dried. The solid thus obtained was dissolved in a mixture of saturated aqueous sodium bicarbonate solution (420 ml.) and water (420 ml.), treated with charcoal and filtered. The filtrate was acidified by the dropwise addition, with stirring, of concentrated hydrochloric acid until the powdery precipitate began to become sticky. The addition of a little 2N aqueous sodium carbonate solution removed this stickiness and a white powdery solid was collected, washed with water and dried to give 5-(2-methylbenzyl)-furoic acid (39 g.), m.p. 136°-138° C., raised to 139°-141° C. by recrystallisation from light petroleum (b.p. 100°-120° C.).

Workup

  1. temperatureThe mixture was gradually warmed
  2. temperaturemaintained
  3. customby collecting the gas over water
  4. temperatureThe reaction mixture was cooled
  5. additiondiluted with water (600 ml.)
  6. additionwhile acidifying by dropwise addition of concentrated hydrochloric acid
  7. customto give crude 5-(2- methylbenzyl)-2-furoic acid in the form of a sticky, brown coloured solid, which
  8. customwas collected
  9. washwashed with water
  10. customdried
  11. customThe solid thus obtained
  12. filtrationfiltered
  13. additionThe filtrate was acidified by the dropwise addition
  14. stirringwith stirring, of concentrated hydrochloric acid until the powdery precipitate
  15. additionThe addition of a little 2N aqueous sodium carbonate solution
  16. customremoved this stickiness
  17. customa white powdery solid was collected
  18. washwashed with water
  19. customdried

Sources & evidence

ORD record
ord-b8d09c2c9be7442bab9bebcc016c2c55
Source dataset
uspto-grants-1978_01
Patent number
US04067723

Reaction notes

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