Benzaldehyde → HCID 212553, compound

HRID 2113926Notes

Reaction equation

HRID 2113926 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=O)[CH2:11][CH2:10]1.Cl>C(O)C>[CH:12](=[C:11]1[C:1](=[O:8])[C:2]2[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:9][CH2:10]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 68110Chromanone

Product 1

HCID 212553HCID 212553, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(66) To a solution of benzaldehyde (430 mg, 4.05 mmol) and 4-chromanone (500 mg, 3.37 mmol) in 8.4 ml of ethanol heated almost to boiling was added 1.7 ml of concentrated hydrochloric acid dropwise. After refluxing for 2 days, the solution was cooled overnight, and a precipitate formed. The precipitate was recrystallized from ethanol to afford 367 mg (46.1%) of white flakes: mp 111.8-113.4° C. (lit. mp 112° C., Powell, J. Am. Chem. Soc., 1923, 45, 2708-2711). 1H NMR (250 MHz) δ 8.06-8.02 (dd, 1H), 7.90 (s, 1 H), 7.54-7.31 (m, 6 H), 7.09 (t, 1 H), 7.00-6.96 (d, 1 H), 5.37 (s, 2 H); 13C NMR (62.7 MHz) 182.4, 161.3, 137.7, 136.1, 134.6, 131.1, 130.2, 129.7, 128.9, 128.1, 122.1, 118.1, 67.8 ppm.

Workup

  1. temperatureAfter refluxing for 2 days
  2. temperaturethe solution was cooled overnight
  3. customa precipitate formed
  4. customThe precipitate was recrystallized from ethanol
  5. customto afford 367 mg (46.1%) of white flakes

Sources & evidence

ORD record
ord-9b5246734b344248b0fb5313b5405ee9
Source dataset
uspto-grants-2008_10
Patent number
US07432303B2

Reaction notes

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