Hydrochloric Acid → 4-[4-(Decyloxy)-3-fluorophenyl]-benzoic acid

HRID 1165731ノート

反応式

HRID 1165731 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[CH2:18](Br)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[OH-].[Na+].Cl>C(O)C>[CH2:18]([O:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][CH:10]=2)=[CH:3][C:2]=1[F:1])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 81731-BromodecaneHCID 14798Sodium HydroxideHCID 8361394-(3-Fluoro-4-hydroxyphenyl)benzoic acid

生成物 1

HCID 147456314-[4-(Decyloxy)-3-fluorophenyl]-benzoic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

The resulting 3'-fluoro-4'-hydroxybiphenyl-4-carboxylic acid was heated under reflux for 10 hours in hydrous ethanol together with 1.2 moles, per mole of the carboxylic acid, of decyl bromide and 1.95 moles, per mole of the carboxylic acid, of sodium hydroxide. Then, 10% hydrochloric acid was added to adjust the pH of the solution to 2 to 3. The solution was then heated under reflux for 1 hour. After cooling, the organic materials were extracted with chloroform. The chloroform layer was washed with water and dried over anhydrous sodium sulfate. The chloroform layer was concentrated to obtain crude crystals. Recrystallization from ethanol gave the desired 4'-decyloxy-3'-fluorobiphenyl-4-carboxylic acid. The yield in this alkoxylation reaction slightly varies depending upon the type of the alkyl bromide used, but it is generally 60 to 80%.

後処理

  1. temperatureThe solution was then heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. extractionthe organic materials were extracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe chloroform layer was concentrated
  8. customto obtain crude crystals
  9. customRecrystallization from ethanol

出典と根拠

ORDレコード
ord-96975ec4a9ab44a984a98b5c2f251512
出典データセット
uspto-grants-1990_03
特許番号
US04911862

反応ノート

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