Sulfuric Acid → 4-n-Decyloxy-1-naphthol

HRID 904715

反応式

HRID 904715 の反応式
[CH:1]1[CH:6]=[C:5]2[C:7]([OH:12])=[CH:8][CH:9]=[C:10]([OH:11])[C:4]2=[CH:3][CH:2]=1.[CH2:13](O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].S(=O)(=O)(O)O>C(OCC)(=O)C.O>[CH2:13]([O:12][C:7]1[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:10]([OH:11])=[CH:9][CH:8]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 81741-DecanolHCID 113051,4-Naphthalenediol

生成物 1

HCID 204786024-n-Decyloxy-1-naphthol

試薬・触媒・溶媒 1

HCID 22728543Water ethylacetate溶媒

反応条件

温度
50 °C

実験手順

112 g of naphthohydroquinone and 560 ml of n-decanol were placed in a 1 l three-necked flask and 56 ml of concentrated sulfuric acid was dropwisely added thereto for 30 minutes under nitrogen gas stream while stirring. Thereafter, the mixture was further stirred for 30 minutes and, then, heated at 50° C. for 1 hour and 30 minutes. After cooling, ethyl acetate-water was added to the reaction mixture and the precipitated crystals were filtered off. An aqueous sodium hydroxide solution was added to the filtrate so as to water layer reach pH of 5 to 6. Then, the ethyl acetate layer was washed with water and dried with MgSO4 overnight. The dried ethyl acetate solution was evaporated under reduced pressure to remove ethyl acetate and n-decanol. The residue was dissolved in 1 l of ethyl acetate and treated with 26 g of active carbon followed by concentration under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate and n-hexane and, further, recrystallized from benzene to obtain 73 g of white crystals having a melting point of 89° to 90° C.

後処理

  1. stirringThereafter, the mixture was further stirred for 30 minutes
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were filtered off
  4. additionAn aqueous sodium hydroxide solution was added to the filtrate so as to water layer
  5. washThen, the ethyl acetate layer was washed with water
  6. dry with materialdried with MgSO4 overnight
  7. customThe dried ethyl acetate solution was evaporated under reduced pressure
  8. customto remove ethyl acetate and n-decanol
  9. dissolutionThe residue was dissolved in 1 l of ethyl acetate
  10. additiontreated with 26 g of active carbon
  11. concentrationfollowed by concentration under reduced pressure
  12. customThe residue was recrystallized from a mixed solvent of ethyl acetate and n-hexane
  13. customfurther, recrystallized from benzene

出典と根拠

ORDレコード
ord-06aca79e44b540eca28112d276125b00
出典データセット
uspto-grants-1983_12
特許番号
US04419439

関連ノート

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