HCID 22729428, compound → HCID 23245499, compound

HRID 2085426Notes

Reaction equation

HRID 2085426 reaction equation
[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[CH2:12][CH2:13][OH:14]>C(Cl)Cl.O=[Mn]=O>[OH:14][CH2:13][CH2:12][CH:3]1[CH2:4][CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]1=[O:1]

Participants

4

Reactant 1

HCID 22729428HCID 22729428, compound

Product 1

HCID 23245499HCID 23245499, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of isomeric mixture of 1-hydroxyl-2-(2-hydroxyethyl)-1,2,3,4-tetrahydronaphthalene (3.00 g, 15.6 mmol) in CH2Cl2 (100 mL) was treated with MnO2 (20.4 g, 0.234 mole). The suspension was stirred at room temperature for 16 h and the solids were removed by filtration. Concentration of the filtrate in vacuo gave a brown oil, which was further purified by flash chromatography (MeOH/CHCl3, 5/95), giving a yellow oil (2.00 g, 67.4%): 1H NMR δ 1.76 (m, 1H), 1.98 (m, 1H), 2.21 (m, 2H), 2.57 (br, 1H), 2.70 (m, 2H), 3.20 (m, 2H), 3.81 (m, 2H), 7.00-8.20 (m, 4H); CI mass spectrum (M+1)+ at m/z 191.

Workup

  1. customthe solids were removed by filtration
  2. customConcentration of the filtrate in vacuo gave a brown oil, which
  3. customwas further purified by flash chromatography (MeOH/CHCl3, 5/95)

Sources & evidence

ORD record
ord-be1ca387175548e296d7a758704a3cd3
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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