HCID 18420342, compound → HCID 23390599, compound

HRID 990321Notes

Reaction equation

HRID 990321 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][CH:12]([OH:21])[C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]>ClCCl.[O-2].[O-2].[Mn+4]>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12](=[O:21])[C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 18420342HCID 18420342, compound

Product 1

HCID 23390599HCID 23390599, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

C20H16O, FW=272.34 g/mol. 1-(4-Isopropylphenyl)-5-phenyl-1,4-pentadiyn-3-ol (5.65 g, 20.6 mmol) and manganese dioxide (10.74 g, 124 mmol) were combined in dichloromethane (41 mL) and heated to reflux for 30 minutes. Following completion of the reaction, the reaction mixture is filtered through celite, concentrated and the orange liquid product is isolated in 92% yield. Rf 0.87 (DCM) 1H NMR (500 MHz, CDCl3, ppm) d 7.63 (d, 2H, J=7.0 Hz), 7.57 (d, 2H, J=8.4 Hz), 7.46 (d, 1H, J=7.3 Hz), 7.40 (d, 2H, J=7.7 Hz), 7.29 (Ar, m, 2H) 2.93 (m, 1H), 1.24 (d, 6H, J=7.0 Hz); HR MS (EI) m/z calculated 272.120115, found 272.119612.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 minutes
  3. customcompletion of the reaction
  4. filtrationthe reaction mixture is filtered through celite,
  5. concentrationconcentrated
  6. customthe orange liquid product is isolated in 92% yield

Sources & evidence

ORD record
ord-b0268fe60c0e4481826a91029994c6e3
Source dataset
uspto-grants-2002_10
Patent number
US06458967B1

Reaction notes

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