Ethanol → 4'-(Hexyloxy)[1,1'-biphenyl]-4-ol

HRID 260015

反応式

HRID 260015 の反応式
[C:1]1(O)[C:2]([C:7]2[C:8](O)=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:3][CH:4]=[CH:5][CH:6]=1.[OH-:15].[Na+].Br[CH2:18][CH2:19][CH2:20][CH2:21]CC.[CH2:24]([OH:26])[CH3:25]>>[CH2:24]([O:26][C:5]1[CH:4]=[CH:3][C:2]([C:7]2[CH:8]=[CH:9][C:10]([OH:15])=[CH:11][CH:12]=2)=[CH:1][CH:6]=1)[CH2:25][CH2:18][CH2:19][CH2:20][CH3:21]

参加物

5

反応物 4

HCID 702EthanolHCID 81011-BromohexaneHCID 14798Sodium HydroxideHCID 15731(1,1'-Biphenyl)-2,2'-diol

生成物 1

HCID 138784254'-(Hexyloxy)[1,1'-biphenyl]-4-ol

実験手順

A mixture of 74 g (0.40 moles) of biphenol and 20 g (0.50 moles) of sodium hydroxide in 600 ml of ethanol was refluxed for 1 hour. At reflux temperature 66 g (0.40 moles) of 6-bromohexane were added over a period of 1 hour. The reaction mixture was refluxed for 18 hours and cooled to room temperature, and the precipitate was filtrated. The filtrate was treated with 500 ml of water and the precipitated 4-hexyloxy-4'-hydroxybiphenyl was filtrated and washed with water. After drying 29 g of product were obtained. An additional amount of product was obtained by refluxing the precipitate collected from the reaction mixture with 45 g of potassium hydroxide in 600 ml of ethanol for 3 hours. This mixture was cooled to room temperature and the insoluble dihexyloxybiphenyl filtered off. The clear filtrate was treated with 200 ml of 6N hydrochloric acid and the precipitated 4-hexyloxy-4'-hydroxybiphenyl was filtrated, washed with water, and dried. The yield was 19 g. The total yield was 48 g (44% of theory).

後処理

  1. temperaturewas refluxed for 1 hour
  2. additionwere added over a period of 1 hour
  3. temperatureThe reaction mixture was refluxed for 18 hours
  4. filtrationthe precipitate was filtrated
  5. additionThe filtrate was treated with 500 ml of water
  6. filtrationthe precipitated 4-hexyloxy-4'-hydroxybiphenyl was filtrated
  7. washwashed with water
  8. dry with materialAfter drying 29 g of product
  9. customwere obtained
  10. customAn additional amount of product was obtained
  11. temperatureby refluxing the precipitate
  12. customcollected from the reaction mixture with 45 g of potassium hydroxide in 600 ml of ethanol for 3 hours
  13. temperatureThis mixture was cooled to room temperature
  14. filtrationthe insoluble dihexyloxybiphenyl filtered off
  15. additionThe clear filtrate was treated with 200 ml of 6N hydrochloric acid
  16. filtrationthe precipitated 4-hexyloxy-4'-hydroxybiphenyl was filtrated
  17. washwashed with water
  18. customdried

出典と根拠

ORDレコード
ord-78f873dc49b64b85b5095e8e67be0a3e
出典データセット
uspto-grants-1996_06
特許番号
US05525265

関連ノート

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