Ethylene Glycol → 4-(2'-Hydroxyethoxy)-2-methyl-1-hydroxynaphthalene

HRID 1003122

反応式

HRID 1003122 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.[CH2:19](O)[CH2:20][OH:21]>[Zn].C1(C)C=CC=CC=1>[OH:21][CH2:20][CH2:19][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 174Ethylene GlycolHCID 1118Sulfuric AcidHCID 4055Menadione

生成物 1

HCID 158473234-(2'-Hydroxyethoxy)-2-methyl-1-hydroxynaphthalene収率 70%

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) 2-methyl-1,4 naphthoquinone, 2.71 g (41.4 mmole) of zinc powder, 15 mL of ethylene glycol and 15 mL of toluene in an ice bath. After the addition was complete, the reaction mixture was stirred for 5 hours at 100° C. The reaction product was extracted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered, then evaporated under reduced pressure to give 4.21 g (70% yield) of the above product. That product had a melting point of 136.3-136.8° C. and an 1HNMR as follows: (300 MHz, DMSO-d6) δ 2.37 (s, 3H), 3.86 (m, 2H), 4.10 (t, 2H, J=4.8 Hz), 4.98 (t, 1H, J=5.4 Hz), 6.76 (s, 1H), 7.42 (m, 2H), 8.14 (d, 1H, J=9.0 Hz), 8.17 (d, 1H, J=9.0 Hz), 8.51 (s, 1H). The mass spectrum showed a molecular ion at m/z 218.

後処理

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

出典と根拠

ORDレコード
ord-55b90b1bffb049339a18b2891379a7c2
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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