Benzaldehyde → 2-Benzylidene-3,4-dihydronaphthalen-1-one

HRID 576488Notes

Reaction equation

HRID 576488 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[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[K+]>O1CCCC1.CO>[CH:12](=[C:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]1=[O:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 107241-TetraloneHCID 14797Potassium Hydroxide

Product 1

HCID 1111792-Benzylidene-3,4-dihydronaphthalen-1-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 250 mL flask was charged with tetralone (4 g, 27.4 mmol) and benzaldehyde (3.88 g, 36.6 mmol). This was dissolved in warm tetrahydrofuran (15 mL), and to this yellow solution was slowly added a 4 wt % solution of KOH in methanol (125 mL). The reaction was stirred for 4 days at room temperature. The solvent was then removed under reduced pressure, and it was poured into 150 mL of water and extracted with methylene chloride. The organic extract was dried over magnesium sulfate and filtered, and the solvent was removed at reduced pressure to afford 4.1 g (64%) as white powder.

Workup

  1. customThe solvent was then removed under reduced pressure, and it
  2. additionwas poured into 150 mL of water
  3. extractionextracted with methylene chloride
  4. extractionThe organic extract
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed at reduced pressure
  8. customto afford 4.1 g (64%) as white powder

Sources & evidence

ORD record
ord-bf428d9552f342caab4e5241e9dfdf60
Source dataset
uspto-grants-2015_05
Patent number
US09040175B2

Reaction notes

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