2-[2-(Hydroxymethyl)phenyl]ethanol → 3,4-Dihydro-1H-2-benzopyran-1-ol

HRID 553285

Reaction equation

HRID 553285 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][OH:11]>ClCCl.[O-2].[Mn+4].[O-2]>[CH:2]1([OH:1])[C:3]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:9][CH2:10][O:11]1

Participants

4

Reactant 1

HCID 2390242-[2-(Hydroxymethyl)phenyl]ethanol

Product 1

HCID 136137083,4-Dihydro-1H-2-benzopyran-1-olYield 53.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese(IV) oxide (1.43 g) was added to a solution of 2-(2-hydroxymethyl-phenyl)-ethanol (0.5 g) in dichloromethane (25 mL) and stirred for 18 hours under nitrogen. The reaction was filtered through celite, the filter pad washed with dichloromethane (2×20 mL), and the combined filtrates evaporated. Purification on silica, eluting with a gradient of iso-hexane:ethyl acetate [1:0 to 4:1], afforded the subtitle compound as a yellow oil (263 mg).

Workup

  1. filtrationThe reaction was filtered through celite
  2. washthe filter pad washed with dichloromethane (2×20 mL)
  3. customthe combined filtrates evaporated
  4. customPurification on silica
  5. washeluting with a gradient of iso-hexane

Sources & evidence

ORD record
ord-5b9ef1618df74ec89cec983bf8208578
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Linked notes

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