Sulfuric acid magnesium salt (1:1) → HCID 18357908, compound

HRID 428227Notes

Reaction equation

HRID 428227 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH2:14][C:15]#[C:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.S([O-])([O-])(=O)=O.[Mg+2]>[O-2].[Mn+2].ClCCl>[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH2:14][C:15]#[C:16][C:17]3[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 2

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 18357935HCID 18357935, compound

Product 1

HCID 18357908HCID 18357908, compound

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

1.3 g (4 mmol) of 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzenemethanol and 20 ml of dichloromethane are introduced into a round-bottomed flask and 3.4 g (39.2 mmol) of manganese oxide are added. The mixture is stirred at room temperature for eight hours. Magnesium sulphate is added to the reaction medium, the mixture is filtered and the filtrate is evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of ethyl acetate and heptane (10/90). After evaporation of the solvents, 930 mg (29.5%) of 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzaldehyde are collected in the form of a yellow oil.

Workup

  1. filtrationthe mixture is filtered
  2. customthe filtrate is evaporated
  3. customThe residue obtained
  4. customis purified by chromatography on a column of silica
  5. washeluted with a mixture of ethyl acetate and heptane (10/90)
  6. customAfter evaporation of the solvents, 930 mg (29.5%) of 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzaldehyde
  7. customare collected in the form of a yellow oil

Sources & evidence

ORD record
ord-c714f0b04ee14e40b54cea5db4dae936
Source dataset
uspto-grants-2001_11
Patent number
US06313162B1

Reaction notes

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