Sodium Bicarbonate → 7-Methoxynaphthalene-1-carbaldehyde

HRID 551777Notes

Reaction equation

HRID 551777 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH:13]=C)=[CH:5][CH:4]=1.I([O-])(=O)(=O)=[O:16].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH:13]=[O:16])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 445416687-Methoxy-1-vinylnaphthalene

Product 1

HCID 157882797-Methoxynaphthalene-1-carbaldehyde

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

The compound obtained in Step B (13.4 mmol) and osmium tetroxide (0.16 mmol) are dissolved in 70 ml of a mixture of tetrahydrofuran/water (1/1). Sodium periodate (26.9 mmol) is added in small portions and the reaction mixture is stirred for 2 hours at ambient temperature. The reaction mixture is poured into 50 ml of 5% sodium hydrogen carbonate solution, the insoluble material is filtered off and the aqueous phase is extracted twice with 75 ml of ether. The organic phase is washed with water, decolourised and evaporated. The precipitate obtained is recrystallised from cyclohexane and yields the title product in the form of a white solid.

Workup

  1. filtrationthe insoluble material is filtered off
  2. extractionthe aqueous phase is extracted twice with 75 ml of ether
  3. washThe organic phase is washed with water
  4. customevaporated
  5. customThe precipitate obtained
  6. customis recrystallised from cyclohexane

Sources & evidence

ORD record
ord-e06ce472994a4ea1acc720473797df9e
Source dataset
uspto-grants-2011_05
Patent number
US07947852B2

Reaction notes

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