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

HRID 324236

反応式

HRID 324236 の反応式
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

参加物

4

反応物 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2 回HCID 2365474,4-Dimethyl-3,4-dihydro-2H-naphthalen-1-one

生成物 1

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

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-1307f27a40154de1bcbfb521e53e0d08
出典データセット
uspto-grants-2001_04
特許番号
US06218128B1

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