Nitric Acid → 4,4-Dimethyl-7-nitro-3,4-dihydronaphthalen-1(2H)-one

HRID 324236

반응식

HRID 324236 반응식
OS(O)(=O)=O.[CH3:6][C:7]1([CH3:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[CH2:9][CH2:8]1.[N+:19]([O-])([OH:21])=[O:20]>>[CH3:6][C:7]1([CH3:18])[C:16]2[C:11](=[CH:12][C:13]([N+:19]([O-:21])=[O:20])=[CH:14][CH:15]=2)[C:10](=[O:17])[CH2:9][CH2:8]1

참가 물질

4

반응물 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2회HCID 2365474,4-Dimethyl-3,4-dihydro-2H-naphthalen-1-one

생성물 1

HCID 134632924,4-Dimethyl-7-nitro-3,4-dihydronaphthalen-1(2H)-one

실험 절차

To 1.7 ml (3.0 g, 30.6 mmol, 18M) H2SO4 at −5° C. (ice-NaCl bath) was slowly added 783.0 mg (4.49 mmol) of 3,4-dihydro-4,4-dimethyl-1(2H)-naphthalenone. A solution of 426.7 mg (6.88 mmol, 0.43 ml, 16M) HNO3, and 1.31 g (0.013 mol, 0.74 ml, 18 M) H2SO4 was slowly added. After 20 minutes, ice was added and the resulting mixture extracted with EtOAc. The combined extracts were concentrated under reduced pressure to give a residue from which the title compound, a pale yellow solid, was isolated by column chromatography (10% EtOAC/hexanes). 1H NMR (CDCl3): δ 8.83 (1H, d, J=2.6 Hz), 8.31 (1H, dd, J=2.8, 8.9 Hz), 7.62 (1H, d, J=8.7 Hz), 2.81 (2H, t, J=6.5 Hz), 2.08 (2H, t, J=6.5 Hz), 1.45 (6H, s).

후처리

  1. customat −5° C.
  2. additionice was added
  3. extractionthe resulting mixture extracted with EtOAc
  4. concentrationThe combined extracts were concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1307f27a40154de1bcbfb521e53e0d08
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218128B1

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