Hydrochloric Acid → HCID 12906154, compound

HRID 647049Notes

Reaction equation

HRID 647049 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:26])[C:5]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])=[C:6]([CH3:12])[C:7](=[O:11])[C:8]=1[O:9][CH3:10].[OH-].[K+].S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl>C(OCC)C>[CH3:1][O:2][C:3]1[C:4](=[O:26])[C:5]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[C:6]([CH3:12])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24489Sodium DithioniteHCID 12824089HCID 12824089, compound

Product 1

HCID 12906154HCID 12906154, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2,3-dimethoxy-5-methyl-6-(8'-ethoxycarbonyloctyl)-1,4-benzoquinone (formula I-2 wherein R=H3CO, n=7, in the form of ethylester) (0.8 part) in diethyl ether (10 volume parts), followed by the addition of a 30% solution (20 volume parts) of potassium hydroxide containing sodium hydrosulfite. The mixture was refluxed for 1 hour. After cooling, the reaction mixture was rendered acidic with hydrochloric acid and extracted with diethyl ether. The ethereal extract was washed with water and shaken together with a solution of ferric chloride. The ethereal layer was washed with water and dried over anhydrous sodium sulfate. The diethyl ether was distilled off under reduced pressure and the resulting residue was crystallized from diethyl ether-hexane. The procedure provided 2,3-dimethoxy-5-methyl-6-(8'-carboxyoctyl)-1,4-benzoquinone (formula I-2 wherein R=H3CO, n=7, in the free form) (0.53 part) as orange-colored needles melting at 39°-40.5° C.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. extractionextracted with diethyl ether
  4. extractionThe ethereal extract
  5. washwas washed with water
  6. washThe ethereal layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe diethyl ether was distilled off under reduced pressure
  9. customthe resulting residue was crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-f793d34cb2774e2c937b2da5bea0e0e4
Source dataset
uspto-grants-1983_10
Patent number
US04407757

Reaction notes

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