Hydrochloric Acid → Methyl 4-[(2-benzyloxyphenyl)hydroxymethyl]benzoate

HRID 1247713ノート

反応式

HRID 1247713 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[CH:17]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)=[O:18].Cl>O1CCCC1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:17]([OH:18])[C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 15294Methyl 4-FormylbenzoateHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 5462224Magnesium

生成物 1

HCID 21909317Methyl 4-[(2-benzyloxyphenyl)hydroxymethyl]benzoate収率 37.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A Grignard reagent was prepared from 1-benzyloxy-2-bromobenzene (5.3 g), magnesium (0.49 g) and tetrahydrofuran (160 mL). The obtained Grignard reagent was added to a solution of methyl 4-formylbenzoate (3.3 g) in tetrahydrofuran (60 mL), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture were added water and dilute hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on aminopropyl silica gel (eluent: hexane/ethyl acetate=4/1) to give methyl 4-[(2-benzyloxyphenyl)hydroxymethyl]benzoate (2.6 g).

後処理

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on aminopropyl silica gel (eluent: hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-b486ce6bb6104e96b7bcf83152c48c29
出典データセット
uspto-grants-2006_10
特許番号
US07129381B2

反応ノート

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