Triacetoxyperiodinane → 8-Methyl-1,2,3,4-tetrahydronaphthalene-1-carbaldehyde

HRID 1623033Notes

Reaction equation

HRID 1623033 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]([CH2:12][OH:13])[CH2:9][CH2:8][CH2:7]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]([CH:12]=[O:13])[CH2:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 118052711,2,3,4-Tetrahydro-8-methyl-1-naphthalenemethanol

Product 1

HCID 220221828-Methyl-1,2,3,4-tetrahydronaphthalene-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(8-Methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-methanol (0.03 g, 0.17 mmol) was dissolved in dichloromethane (0.5 mL). To the solution was then added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one, also known as Dess-Martin periodinane (0.087 g, 0.20 mmol). The reaction mixture was stirred for 2 hrs then partitioned with an aqueous saturated solution of thiosulfate and dichloromethane. The organic layer was washed with an aqueous saturated solution of thiosulfate, an aqueous saturated solution of sodium bicarbonate, brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield 8-methyl-1,2,3,4-tetrahydro-naphthalene-1-carbaldehyde as a solid.

Workup

  1. customthen partitioned with an aqueous saturated solution of thiosulfate and dichloromethane
  2. washThe organic layer was washed with an aqueous saturated solution of thiosulfate
  3. dry with materialan aqueous saturated solution of sodium bicarbonate, brine, dried with Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-324d17e9bb554dce8b9742ae7241971b
Source dataset
uspto-grants-2014_07
Patent number
US08778956B2

Reaction notes

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