Sodium Dithionite → 2,6-Dimethylhydroquinone

HRID 2399180Notes

Reaction equation

HRID 2399180 reaction equation
[CH3:1][C:2]1[C:3](=[O:10])[C:4]([CH3:9])=[CH:5][C:6](=[O:8])[CH:7]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CCOCC>[OH:10][C:3]1[C:4]([CH3:9])=[CH:5][C:6]([OH:8])=[CH:7][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 682412,6-Dimethyl-1,4-benzoquinone

Product 1

HCID 695602,6-Dimethylhydroquinone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2,6-dimethyl-1,4-benzoquinone (Xa) (5.66g, 42 mmol, Aldrich) in Et2O (200 mL) was shaken vigorously in a separatory funnel with two 200 mL portions of aqueous sodium hydrosulfite solution (sodium dithionite, Na2S2O4, 14.5 g, 83.3 mmol) until the Et2O layer turned bright yellow. The ether layer was washed with brine (200 mL×2), dried (MgSO4) and concentrated in vacuo to obtain 4.865g (35.3 mmol, Y: 83.9%) of the title compound as a white solid: mp, 148°-150° C. (acetone-hexane) [mp reported by L. A. Carpino, S. A. Triolo, and R. A. Berglund in J. Org. Chem., 54, 3303 (1989): 145°-148° C.]; Rf 0.47 (10% EtOAc in CH2Cl2); IR(KBr) 3312 cm-1 (OH); 1H-NMR (300 MHz, acetone-d6) δ ppm: 2.15 (6H, s, Me), 6.45 (2H, s, Ar-H), 6.58 (1H, s, OH), 7.47 (1H, s, OH); 13C-NMR (75 MHz, acetone-d6) δ ppm: 16.84, 116.00, 126.45, 147.46, 151.54; MS (isobutane-DCI) m/e 139 (MH+).

Workup

  1. washThe ether layer was washed with brine (200 mL×2)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c171dfdf341b4173bbaf9e51def9c55e
Source dataset
uspto-grants-1995_09
Patent number
USH0001487

Reaction notes

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