Hydrochloric Acid → HCID 10083450, compound

HRID 1165013Notes

Reaction equation

HRID 1165013 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH:12](=O)[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[OH:15].CC(C)([O-])C.[K+].Cl>C(O)(C)(C)C>[OH:15][C:14]1[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=1[CH2:12][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]=1[OH:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 107241-TetraloneHCID 23665647Potassium tert-butoxide

Product 1

HCID 10083450HCID 10083450, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 1-tetralone (5.85 g, 0.040 mole) and salicylaldehyde (4.88 g, 0.040 mole) in t-butanol (400 mL) was treated with potassium t-butoxide (17.6 g, 0.160 mole) and heated at reflux for 16 hours. After cooling to room temperature, the solution was poured into stirred 1.0N hydrochloric acid. After isolation by extraction with ethyl acetate, the crude product was chromatographed with 4:1 petroleum ether/ether, to provide a tan solid. This was recrystallized (cyclohexane/chloroform) to give the title compound as white needles (5.24 g, 52%), mp 124°-125°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. additionthe solution was poured
  4. extractionAfter isolation by extraction with ethyl acetate
  5. customthe crude product was chromatographed with 4:1 petroleum ether/ether
  6. customto provide a tan solid
  7. customThis was recrystallized (cyclohexane/chloroform)

Sources & evidence

ORD record
ord-73768a21f7d54baaa9b93021d196c0ff
Source dataset
uspto-grants-1990_03
Patent number
US04906636

Reaction notes

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