HCID 89649943, compound → HCID 57210661, compound

HRID 1479033Notes

Reaction equation

HRID 1479033 reaction equation
[OH:1][CH2:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[O:5][CH:6]([CH3:9])[CH2:7][OH:8]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[OH:8][CH2:7][CH:6]([CH3:9])[O:5][C:4]1[CH:10]=[CH:11][CH:12]=[CH:13][C:3]=1[CH:2]=[O:1]

Participants

4

Reactant 1

HCID 89649943HCID 89649943, compound

Product 1

HCID 57210661HCID 57210661, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (4.02 g; 26.3 mmol; 5 eq.) was added to a solution of 2-(2-hydroxymethyl-phenoxy)-propan-1-ol (960 mg; 5.3 mmol; 1 eq.) in DCM (50 mL) and the resulting mixture was stirred at room temperature for 1.5 hour. The suspension was filtered through a short plug of Celite®. The solution was washed with water, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (705 mg, 74%) as a colourless oil. UPLC/MS: (MS+) 181.1 ([M+H]+).

Workup

  1. filtrationThe suspension was filtered through a short plug of Celite®
  2. washThe solution was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fc15271e5064eb5b802929bccdc6a4f
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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