Hydrochloric Acid → (biphenyl-4-yloxy)acetic acid

HRID 2269710ノート

反応式

HRID 2269710 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.Br[CH2:17][C:18]([OH:20])=[O:19].Cl>O.CN(C=O)C>[C:7]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([O:3][CH2:17][C:18]([OH:20])=[O:19])=[CH:9][CH:8]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 71034-HydroxybiphenylHCID 24758Sodium hydride

生成物 1

HCID 262285(biphenyl-4-yloxy)acetic acid収率 65.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% dispersion in oil; 0.8 g) was added portionwise to a DMF (10 ml) solution of 4-hydroxybiphenyl (1.7 g) under ice-cooling. The reaction mixture was stirred at room temperature for 30 minutes, to which was added bromoacetic acid (1.4 g). The reaction mixture was further stirred at room temperature for 18 hours, which was poured into water. 2N hydrochloric acid was added to the mixture to adjust the pH to 4, which was extracted with ethyl acetate. The organic layer was washed with water, then dried and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/1), and the crude crystals were recrystallized from IPE to obtain the entitled compound (1.5 g).

後処理

  1. temperaturecooling
  2. stirringThe reaction mixture was further stirred at room temperature for 18 hours
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/1)
  8. customthe crude crystals were recrystallized from IPE

出典と根拠

ORDレコード
ord-684188c482fc4c2c97acb9fa4348a47c
出典データセット
uspto-grants-2001_12
特許番号
US06329389B1

反応ノート

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