Hydrochloric Acid → 2-Chloro-4-(1-hydroxyoctadecyl)benzoic acid

HRID 1381720ノート

反応式

HRID 1381720 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]([C:11](=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[BH4-].[Na+].O.Cl>C(O)C>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([OH:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydride3 回HCID 15592211HCID 15592211、化合物

生成物 1

HCID 565572-Chloro-4-(1-hydroxyoctadecyl)benzoic acid収率 93.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒3 回

実験手順

To 159 mg of product from Example 11 suspended in 10 ml of ethyl alcohol at 0° C. was added 13 mg of sodium borohydride. An additional 10 ml of ethyl alcohol was added and the reaction stirred overnight while allowed to warm to room temperature. An additional 40 mg of sodium borohydride was added followed in about 20 hours by 50 ml of ethanol and 100 mg of sodium borohydride. Stirring was continued for 20 hours whereupon 25 ml of water was added, followed by 20 ml of 10% hydrochloric acid. The organic solvent was removed using a rotary evaporator and the aqueous residue extracted with two 50 ml portions of ethyl ether. The organic extracts were combined, washed with water, dried over sodium sulfate, and filtered. The solvent was removed using a rotary evaporator to give a white solid (150 mg). Recrystallization of the solid from methanol/hexane gave 139 mg of product identical with that disclosed in Example 14 of U.S. Pat. No. 4,469,885.

後処理

  1. stirringStirring
  2. additionwas added
  3. customThe organic solvent was removed
  4. customa rotary evaporator
  5. extractionthe aqueous residue extracted with two 50 ml portions of ethyl ether
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed
  10. customa rotary evaporator

出典と根拠

ORDレコード
ord-24cabdea76cc4411b44ffe99919285d1
出典データセット
uspto-grants-1989_02
特許番号
US04803294

反応ノート

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