Sodium Dithionite → HCID 12824078, compound

HRID 2412835Notes

Reaction equation

HRID 2412835 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:29])[C:5]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27]C)=[O:26])=[C:6]([CH3:12])[C:7](=[O:11])[C:8]=1[O:9][CH3:10].S(S([O-])=O)([O-])=O.[Na+].[Na+]>CCOCC>[C:25]([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:5]1[C:4](=[O:29])[C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[C:7](=[O:11])[C:6]=1[CH3:12])([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 12824087HCID 12824087, compound

Product 1

HCID 12824078HCID 12824078, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

In 200 ml of ether is dissolved 1.5 g of 2,3-dimethoxy-6-(12-methoxycarbonyldodecyl)-5-methyl-1,4-benzoquinone (I:n=12, R=CH3) and the solution is shaken with 75 ml of a 20% aqueous solution of sodium hydrosulfite. The ether layer is separated and concentrated. To the residue are added, under ice-cooling and in a nitrogen gas stream, 5 ml of a 30% aqueous solution of sodium hydrosulfite and 3.5 ml of a 30% aqueous solution of potassium hydroxide. The mixture is warmed at 50° C. for 2.5 hours. After cooling, the reaction mixture is made acidic with cold hydrochloric acid and extracted with ether. The ether is distilled off under reduced pressure, the residue dissolved in 75 ml of methanol and a solution of 15 g of ferric chloride in 60 ml of water added. The mixture is stirred at room temperature for 1 hour, at the end of which time it is diluted with water and extracted with ethyl acetate. The extract is washed with water and dried, and the solvent is distilled off under reduced pressure. The residue is crystallized from ether-hexane to obtain 1.09 g of 6-(12-carboxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (I:n=12, R=H), m.p. 62° C.

Workup

  1. customThe ether layer is separated
  2. concentrationconcentrated
  3. additionTo the residue are added, under ice-
  4. temperaturecooling and in a nitrogen gas stream, 5 ml of a 30% aqueous solution of sodium hydrosulfite and 3.5 ml of a 30% aqueous solution of potassium hydroxide
  5. temperatureAfter cooling
  6. extractionextracted with ether
  7. distillationThe ether is distilled off under reduced pressure
  8. dissolutionthe residue dissolved in 75 ml of methanol
  9. additiona solution of 15 g of ferric chloride in 60 ml of water added
  10. additionis diluted with water
  11. extractionextracted with ethyl acetate
  12. washThe extract is washed with water
  13. customdried
  14. distillationthe solvent is distilled off under reduced pressure
  15. customThe residue is crystallized from ether-hexane

Sources & evidence

ORD record
ord-339674ded4404dfcb18036836794da5c
Source dataset
uspto-grants-1985_01
Patent number
US04495104

Reaction notes

Loading…