(3,6-Dimethyl-1,2-phenylene)dimethanol → 4,7-Dimethyl-3H-isobenzofuran-1-one

HRID 1879525Notes

Reaction equation

HRID 1879525 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([CH3:10])[C:4]=1[CH2:11][OH:12]>[O-2].[Mn+4].[O-2].ClCCl>[CH3:9][C:8]1[CH:7]=[CH:6][C:5]([CH3:10])=[C:4]2[C:3]=1[CH2:2][O:1][C:11]2=[O:12]

Participants

4

Reactant 1

HCID 13220177(3,6-Dimethyl-1,2-phenylene)dimethanol

Product 1

HCID 5839124,7-Dimethyl-3H-isobenzofuran-1-oneYield 92%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A 1 L 3-necked RBF is charged with 1,2-bis(hydroxymethyl)-3,6-dimethyl-benzene 3 (22.05 g, 0.133 mol), activated 85% manganese(IV) oxide (135.69 g, 1.327 mol), 4 Å molecular sieves (12.00 g) and anhydrous dichloromethane (500 mL), and placed under nitrogen. The reaction mixture is heated to reflux and stirred for 22 h. The reaction mixture is filtered through Kieselguhr and washed thoroughly with dichloromethane. The filtrate is concentrated in vacuo to yield the product 4 as a cream solid (19.79 g, 92%): 1H-NMR (300 MHz, CDCl3) δ 7.31 (d, 1H, 3J=7.5 Hz), 7.18 (d, 1H, 3J=7.5 Hz), 5.18 (s, 2H), 2.65 (s, 3H), 2.29 (s, 3H); 13C-NMR (75 MHz, CDCl3) δ 171.7, 145.8, 136.9, 134.5, 130.8, 129.3, 122.9, 68.3, 16.96, 16.91.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. filtrationThe reaction mixture is filtered through Kieselguhr
  4. washwashed thoroughly with dichloromethane
  5. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-e7245aecc2e24e989bb4edf0e5e8c72e
Source dataset
uspto-grants-2012_11
Patent number
US08318048B2

Reaction notes

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