1-Tetralone → (2E)-3,4-Dihydro-2-[(4-methoxyphenyl)methylene]-1(2H)-naphthalenone

HRID 576494Notes

Reaction equation

HRID 576494 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[C:11]1(=[O:21])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1.[OH-].[K+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[C:12]2/[C:11](=[O:21])[C:20]3[C:15]([CH2:14][CH2:13]/2)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 107241-TetraloneHCID 14797Potassium HydroxideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 695537(2E)-3,4-Dihydro-2-[(4-methoxyphenyl)methylene]-1(2H)-naphthalenoneYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of p-methoxybenzaldehyde (10.00 g, 73.4 mmol, 1.3 eq) and 1-tetralone (8.24 g, 56.4 mmol, 1 eq) was dissolved in tetrahydrofurane (30 mL) and a methanolic solution of potassium hydroxide (4% solution, 250 mL, 7.9 g KOH, 141 mmol, 2.5 eq) was added dropwise over a 15 minutes period to the stirred solution. The mixture was stirred at ambient temperature for three days and the formed precipitate was separated by filtration and purified by washing with MTBE. After drying in vacuo a pale yellow solid (8.57 g, 60% yield, GC-MS purity 99%) was obtained. The filtrate was reduced to a quarter of its volume and a second fraction (3.7 g, 26% yield, GC-MS purity 100%) could be isolated after filtration and washing with a low amount of methanol and a higher amount of MTBE. The over-all yield was 86% and the product was directly used in the next step without any further purification.

Workup

  1. customthe formed precipitate was separated by filtration
  2. custompurified
  3. washby washing with MTBE
  4. customAfter drying in vacuo a pale yellow solid (8.57 g, 60% yield, GC-MS purity 99%)
  5. customwas obtained
  6. customa second fraction (3.7 g, 26% yield, GC-MS purity 100%) could be isolated
  7. filtrationafter filtration
  8. washwashing with a low amount of methanol
  9. customThe over-all yield was 86% and the product was directly used in the next step without any further purification

Sources & evidence

ORD record
ord-6645cdca0f194b148a27c3a93e73f420
Source dataset
uspto-grants-2015_05
Patent number
US09040175B2

Reaction notes

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