Sodium Dithionite → 2,6-Dimethylhydroquinone

HRID 327348

반응식

HRID 327348 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 695602,6-Dimethylhydroquinone

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-8134af87778846bd9cf68e5053a6503f
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05272171

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