Hydrochloric Acid → HCID 178439731, compound

HRID 399768Notes

Reaction equation

HRID 399768 reaction equation
[CH:1](=O)[CH2:2][CH3:3].Cl.[CH:6]1[CH:7]=[CH:8][C:9]2[C:16](=[O:17])[C:15]([OH:18])=[CH:14][C:12](=[O:13])[C:10]=2[CH:11]=1>C(O)(=O)C>[OH:18][C:15]1[C:16](=[O:17])[C:9]2[C:10]([C:12](=[O:13])[C:14]=1[CH:1]=[CH:2][CH3:3])=[CH:11][CH:6]=[CH:7][CH:8]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 527Propanal2×HCID 178516607HCID 178516607, compound

Product 1

HCID 178439731HCID 178439731, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Propionaldehyde (RCHO, R=propyl, 5.0 mL, 69.3 mmol) was added to a solution of concentrated HCl (2 mL) and lawsone (2.00 g, 11.5 mmol) in acetic acid (35 mL) at 60° C. After stirring for 1.25 hours, another portion of propionaldehyde was added (5.0 mL, 69.3 mmol). The solution was then stirred for an additional 1 hour. The solution was allowed to cool to room temperature, and then ice water (200 mL) was added to quench the reaction. The solution was extracted with diethyl ether (3×200 mL) and the organic fractions pooled. The combined organic layers were re-extracted with 5% Na2CO3 (8×150 mL). The aqueous extracts were also pooled and acidified with concentrated HCl. A precipitate formed which was collected by filtration to afford (20) as an orange solid. 2-Hydroxy-3-propenyl-1,4-naphthoquinone (20) (983 mg, 40%): mp 133-134° C.; 1H NMR (CDCl3, 300 MHZ) δ 8.13 (d, J=7.7 Hz, 1H), 8.06 (d, J =7.5 Hz, 1H), 7.80-7.62 (m, 3H), 7.15-6.95 (m, 1H), 6.63 (d, J=16.1 Hz, 1H), 1.99 (d, J=6.8 Hz, 3H).

Workup

  1. stirringThe solution was then stirred for an additional 1 hour
  2. customto quench
  3. customthe reaction
  4. extractionThe solution was extracted with diethyl ether (3×200 mL)
  5. extractionThe combined organic layers were re-extracted with 5% Na2CO3 (8×150 mL)
  6. customA precipitate formed which
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-297aae60c5c74585b62dcb5bc516d6e4
Source dataset
uspto-grants-1998_10
Patent number
US05824700

Reaction notes

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