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

HRID 1003644Notes

Reaction equation

HRID 1003644 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]benzene-methanol 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-e5df9574d88c404b80b7db1a0f9dd543
Source dataset
uspto-grants-2000_04
Patent number
US06046220

Reaction notes

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