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4-[4-(1-Adamantyl)-phenoxy]-2-butenoic acid → 4-[4-(1-Adamantyl)-phenoxy]butyric acid

HRID 258984
ノート
印刷プレビュー

反応式

HRID 258984 の反応式
[C:1]12([C:11]3[CH:23]=[CH:22][C:14]([O:15][CH2:16][CH:17]=[CH:18][C:19]([OH:21])=[O:20])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C12(C3C=CC(OC=CCC(O)=O)=CC=3)CC3CC(CC(C3)C1)C2.[H][H]>[Pd].CO>[C:1]12([C:11]3[CH:12]=[CH:13][C:14]([O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:22][CH:23]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 544821354-[4-(1-Adamantyl)-phenoxy]-2-butenoic acidHCID 545391144-[4-(1-Adamantyl)-phenoxy]-3-butenoic acidHCID 178418361HCID 178418361、化合物

生成物 1

HCID 214251534-[4-(1-Adamantyl)-phenoxy]butyric acid

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol
溶媒

実験手順

A solution of 0.9 g of the mixture of 4-[4-(1-adamantyl)-phenoxy]-2-butenoic acid and 4-[4-(1-adamantyl)-phenoxy]-3-butenoic acid is 30 ml of absolute methanol is hydrogenated with 0.3 g of palladium (5% strength on charcoal) until 1 equivalent of hydrogen has been taken up (normal pressure, about 25° C). The catalyst is then filtered off, and the filtrate is mixed with 10 ml of 2 N sodium hydroxide solution and left to stand for 24 hours at about 25° C. It is then evaporated in vacuo to half its volume. The evaporation residue is partitioned between 50 ml of 2 N hydrochloric acid and 3 times 50 ml of methylene chloride. The organic phases are washed until neutral, dried over sodium sulphate and evaporated in vacuo. Crystallisation of the evaporation residue from ethanol gives 4-[4-(1-adamantyl)-phenoxy]butyric acid of melting point 170°-172° C.

後処理

  1. custom(normal pressure, about 25° C)
  2. filtrationThe catalyst is then filtered off
  3. additionthe filtrate is mixed with 10 ml of 2 N sodium hydroxide solution
  4. waitleft
  5. customIt is then evaporated in vacuo to half its volume
  6. customThe evaporation residue is partitioned between 50 ml of 2 N hydrochloric acid and 3 times 50 ml of methylene chloride
  7. washThe organic phases are washed until neutral,
  8. dry with materialdried over sodium sulphate
  9. customevaporated in vacuo
  10. customCrystallisation of the evaporation residue from ethanol

出典と根拠

ORDレコード
ord-c5b93fae33c14131815bb0db3b43ad8c
出典データセット
uspto-grants-1977_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04035413

反応ノート

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