Acetic Acid → 2-(4-tert-butylbenzylidene)-3,4-dihydro-1(2H)-naphthalenone

HRID 1376917Notes

Reaction equation

HRID 1376917 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.[C:12]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].[OH-].[K+].C(O)(=O)C>CO.O>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([CH:20]=[C:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:1]2=[O:11])=[CH:22][CH:23]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 107241-TetraloneHCID 14797Potassium HydroxideHCID 703244-tert-Butylbenzaldehyde

Product 1

HCID 35712132-(4-tert-butylbenzylidene)-3,4-dihydro-1(2H)-naphthalenone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3,4-dihydro-1(2H)-naphthalenone (4.5 g) and 4-tertbutylbenzaldehyde (5.0 g) was stirred with a solution of 4% potassium hydroxide in methanol (100 ml) for 64 hours at room temperature. The mixture was neutralised with glacial acetic acid, followed by dilution with water (100 ml). The resulting copious white precipitate was filtered off, washed with water and dried in vacuo to give 2-(4-tertbutylbenzylidene)-3,4-dihydro-1(2H)-naphthalenone.

Workup

  1. filtrationThe resulting copious white precipitate was filtered off
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-70c289c1c3a14651ab676b8580800073
Source dataset
uspto-grants-1997_09
Patent number
US05663375

Reaction notes

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