Sulfuric Acid → HCID 178442825, compound

HRID 1764310Notes

Reaction equation

HRID 1764310 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([CH:11]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:12]([O:14]CC)=O)=[O:10].S(=O)(=O)(O)[OH:30].[OH-].[Na+]>C(O)C>[CH2:17]([C:11]1[C:12](=[O:14])[C:4]2[C:3]([C:8](=[O:30])[C:9]=1[OH:10])=[C:2]([CH3:1])[CH:7]=[CH:6][CH:5]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 21325239Ethyl 2-[(2-methylphenyl)acetyl]tetradecanoate

Product 1

HCID 178442825HCID 178442825, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Four parts of crude ethyl 2-[(2-methylphenyl)acetyl]tetradecanoate obtained in Example 3 was combined with 12 parts of cold concentrated sulfuric acid and stirred at room temperature for 66 hours. The mixture was poured into ice water and made slightly basic by the addition of 50% aqueous sodium hydroxide. Enough ethanol was added to dissolve the organic matter and air was then bubbled through the solution for 3 hours. The resulting solution was extracted with 100 parts petroleum ether (twice), acidified with hydrochloric acid and re-extracted with diethylether. The ether extract was washed with saturated sodium chloride, dried over magnesium sulfate and evaporated. The residue was taken up in acetonitrile and filtered. The filtrate was evaporated to dryness and the residue triturated with petroleum ether to give 0.2 g of 2-dodecyl-3-hydroxy-5-methyl-1,4-napthoquinone, m.p. 92°-93° C.

Workup

  1. dissolutionto dissolve the organic matter and air
  2. customwas then bubbled through the solution for 3 hours
  3. extractionThe resulting solution was extracted with 100 parts petroleum ether (twice),
  4. extractionre-extracted with diethylether
  5. extractionThe ether extract
  6. washwas washed with saturated sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness
  11. customthe residue triturated with petroleum ether

Sources & evidence

ORD record
ord-ac38cbfad9004ebc8dbacd2a2c56a74d
Source dataset
uspto-grants-1978_09
Patent number
US04115584

Reaction notes

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