4-Hydroxybenzoic Acid → 4-(6-Hydroxyhexyloxy)benzoic acid

HRID 10118

反応式

HRID 10118 の反応式
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.Cl[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18]>[OH-].[K+]>[OH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 1354-Hydroxybenzoic AcidHCID 748286-Chloro-1-hexanol

生成物 1

HCID 36284134-(6-Hydroxyhexyloxy)benzoic acid収率 80%

試薬・触媒・溶媒 1

HCID 14797Potassium Hydroxide溶媒

反応条件

温度
60 °C

実験手順

Monomers in which the bulky organic group was a t-butyl group and the alkyl groups were hexyl groups were made as follows. 4-hydroxybenzoic acid was dissolved in 30% ethanolic KOH. About 1% of KI was added as a catalyst. The mixture was heated to about 60° C. and a stoichiometric amount of 6-chloro-1-hexanol was slowly added over about ½ hour. After refluxing the reaction mixture for extended period of time (2-15 hrs) the contents was cooled, the reaction mixture was filtered off, and the filtrate solvent was evaporated under vacuum. Water was added into the residue and acidified with HCl and the precipitate was filtered and crystallized with ethanol, yielding approximately an 80% 4-(6-hydroxyhexyloxy)-benzoic acid.

後処理

  1. additionAbout 1% of KI was added as a catalyst
  2. temperatureAfter refluxing the reaction mixture for extended period of time (2-15 hrs) the contents
  3. temperaturewas cooled
  4. filtrationthe reaction mixture was filtered off
  5. customthe filtrate solvent was evaporated under vacuum
  6. additionWater was added into the residue
  7. filtrationthe precipitate was filtered
  8. customcrystallized with ethanol

出典と根拠

ORDレコード
ord-dfe4ced729254e01be55cc9bea0175d5
出典データセット
uspto-grants-2006_08
特許番号
US07094358B2

関連ノート

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