Sulfuric Acid → HCID 59378156, compound

HRID 1923467Notes

Reaction equation

HRID 1923467 reaction equation
O=[C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:3]=[CH:4][CH:5]=[CH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.OS(O)(=O)=O>C(O)C.[Pd]>[C:16]1([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]2[CH:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[CH:14][CH:15]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 72281739HCID 72281739, compound

Product 1

HCID 59378156HCID 59378156, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(5-Oxo-5-phenyl-penta-1,3-dienyl)-benzoic acid (13.9 g, 50 mmol) is dissolved in ethanol (280 mL). Concentrated H2SO4 (1 mL) and 5% palladium on carbon (2.8 g) are added and the mixture hydrogenated at 50° C. and 60 psi for 4 h. The reaction is filtered, diluted with water (1000 mL), and extracted several times with diethyl ether. The combined organic extracts are washed with 2 N NaOH. The aqueous portion is acidified with concentrated hydrochloric acid and extracted with diethyl ether. The ether extracts are washed with water, dried over Na2SO4, and evaporated to obtain a solid. The solid is recrystallized from hexanes to obtain 7.2 g (54%) of white crystals. m.p.=80-80.5° C.; Anal. Calcd for C18H20O2: C, 80.56; H, 7.51. Found: C, 80.75; H, 7.34.

Workup

  1. filtrationThe reaction is filtered
  2. additiondiluted with water (1000 mL)
  3. extractionextracted several times with diethyl ether
  4. washThe combined organic extracts are washed with 2 N NaOH
  5. extractionextracted with diethyl ether
  6. washThe ether extracts are washed with water
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. customto obtain a solid
  10. customThe solid is recrystallized from hexanes

Sources & evidence

ORD record
ord-1effdc75052f4fefb47e09514ca53ded
Source dataset
uspto-grants-2012_05
Patent number
US08178528B2

Reaction notes

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