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

HRID 54587

Reaction equation

HRID 54587 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-tert-butylbenzaldehyde (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-tert-butylbenzylidene)-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-392e6da757734f54a4b9ebfe00572a19
Source dataset
uspto-grants-1997_04
Patent number
US05622987

Linked notes

Loading…