Sodium Dithionite → 2,6-Dimethylhydroquinone

HRID 327348

反応式

HRID 327348 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 695602,6-Dimethylhydroquinone

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of 2,6-dimethyl-1,4-benzoquinone (Xa) (5.66 g, 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 4.865 g (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, p. 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+).

後処理

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

出典と根拠

ORDレコード
ord-8134af87778846bd9cf68e5053a6503f
出典データセット
uspto-grants-1993_12
特許番号
US05272171

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