HCID 57475780, compound → HCID 57475783, compound

HRID 2060780Notes

Reaction equation

HRID 2060780 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:15])[CH2:9][CH:10]([OH:14])[CH2:11][CH:12]=[CH2:13])[CH:5]=[CH:6][CH:7]=1>ClCCl.[O-2].[Mn+4].[O-2]>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:15])[CH2:9][CH:10]([OH:14])[CH2:11][CH:12]=[CH2:13])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 57475780HCID 57475780, compound

Product 1

HCID 57475783HCID 57475783, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(3-bromophenyl)hex-5-ene-1,3-diol (2.60 g, 9.59 mmol) and manganese(IV) oxide (9.81 g, 95.9 mmol) in dichloromethane (80 mL) is heated and stirred for 4 h under reflux. The reaction mixture is filtered through a pad of diatomaceous earth and the residue is washed twice with dichloromethane. The filtrate is concentrated under reduced pressure to afford the title compound (2.12 g, 82%). 1H NMR (400 MHz, CDCl3) δ 8.05 (d, 1H, J=1.8 Hz), 7.85 (d, 1H, J=7.5 Hz), 7.69-7.52 (m, 1H), 7.35-7.31 (m, 1H), 5.91-5.82 (m, 1H), 5.18-5.12 (m, 2H), 4.32-4.26 (m, 1H), 3.09-3.00 (m, 2H), 2.39-2.30 (m, 2H).

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. filtrationThe reaction mixture is filtered through a pad of diatomaceous earth
  4. washthe residue is washed twice with dichloromethane
  5. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-913d25feb0324158a215dd8eff622fee
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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