1-(2-Methoxy-4-nitrophenoxy)-2-methylpropan-2-ol → 1-(4-Amino-2-methoxyphenoxy)-2-methylpropan-2-ol

HRID 1916351

反応式

HRID 1916351 の反応式
[CH3:1][O:2][C:3]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][C:7]([CH3:10])([OH:9])[CH3:8]>[Pd].CCO>[NH2:15][C:13]1[CH:12]=[CH:11][C:4]([O:5][CH2:6][C:7]([CH3:10])([OH:9])[CH3:8])=[C:3]([O:2][CH3:1])[CH:14]=1

参加物

4

反応物 1

HCID 588580781-(2-Methoxy-4-nitrophenoxy)-2-methylpropan-2-ol

生成物 1

HCID 595950521-(4-Amino-2-methoxyphenoxy)-2-methylpropan-2-ol

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A stirred EtOH suspension (320 mL) containing 1-(2-methoxy-4-nitrophenoxy)-2-methylpropan-2-ol Part A (13.6 g, 56.4 mmol) and 10% Pd/C (0.25 g) was hydrogenated under 60 psi H2 for 6 hr. HPLC analysis revealed no starting nitro catechol ether remained. The resultant black suspension was filtered through a fiberglass filter paper under a blanket of N2 gas. The resultant clear wine colored solution was immediately concentrated using a rotary evaporator under vacuum to yield 12.4 of desired product as a dark orange oil which was used without further purification. 1H NMR (CDCl3) δ 1.29 (s, 6H), 3.40, (br s, 2H), 3.74 (s, 2H), 3.78 (s, 3H), 6.20 (dd, J=8.35 Hz, 2.64 Hz, 1H), 6.28 (d, J=2.64 Hz, 1H), 6.76 (d, J=8.35 Hz, 1H); 13C NMR (CDCl3) δ 25.90, 55.67, 70.02, 80.30, 100.76, 106.81, 118.27, 141.55, 141.93, 150.99; HPLC (Method #1): 0.88 min retention time; LCMS (ES): m/z 212.1 [M+H].

後処理

  1. filtrationThe resultant black suspension was filtered through a fiberglass
  2. filtrationfilter paper under a blanket of N2 gas
  3. concentrationThe resultant clear wine colored solution was immediately concentrated
  4. customa rotary evaporator under vacuum

出典と根拠

ORDレコード
ord-c8224e73b1874fc8a26e809a58bca65e
出典データセット
uspto-grants-2013_12
特許番号
US08618115B2

関連ノート

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