Sulfuric Acid → 4-(2'-Methoxyethoxy)-2-methyl-1-naphthol

HRID 1003123

反応式

HRID 1003123 の反応式
S(=O)(=O)(O)O.[CH3:6][C:7]1[C:8](=[O:18])[C:9]2[C:14]([C:15](=[O:17])[CH:16]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.[CH3:19][O:20][CH2:21][CH2:22]O>[Zn].C1(C)C=CC=CC=1>[CH3:19][O:20][CH2:21][CH2:22][O:17][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:18])=[C:7]([CH3:6])[CH:16]=1

参加物

6

反応物 3

HCID 1118Sulfuric AcidHCID 4055MenadioneHCID 80192-Methoxyethanol

生成物 1

HCID 158473244-(2'-Methoxyethoxy)-2-methyl-1-naphthol収率 76%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

4.9g of concentrated sulfuric acid were added dropwise, with stirring, to a mixture of 4.75 g (27.6 mmole) of 2-methyl-1,4-naphthoquinone, 2.71 g (41.4 mmole) of zinc powder, 15 mL of 2-methoxyethanol and 15 mL of toluene, in an ice bath. After the addition was completed, the reaction mixture was stirred for 5 hours at 100° C. The reaction product was extracted with ethyl acetate, washed with water, then brine, dried over sodium sulfate, filtered, then evaporated under reduced pressure to give 4.87 g (76% yield) of the title compound. The resultant product had a melting point of 100-101° C. and an 1HNMR as follows: (300 Hz, DMSO-d6) δ 2.33 (s, 3H), 3.34 (s, 3H), 3.79 (t, 2H, J=4.5 Hz), 4.21 (t, 2H, J=4.5 Hz), 6.78(s, 1H), 7.47 (m, 2H), 8.08 (d, 1H, J=8.0 Hz), 8.14 (d, 1H, J=8.0 Hz), 8.54 (s, 1H). The mass spectrum showed a molecular ion at m/z 232.

後処理

  1. additionAfter the addition
  2. extractionThe reaction product was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialbrine, dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-a56c081f340f4d13bbd2530e7e99a1fc
出典データセット
uspto-grants-2000_04
特許番号
US06045590

関連ノート

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