4-Hydroxybenzaldehyde → 4-(Cyclobutylmethoxy)benzaldehyde

HRID 1485057ノート

反応式

HRID 1485057 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.Br[CH2:13][CH:14]1[CH2:17][CH2:16][CH2:15]1.Cl>CN(C)C=O.C(OCC)(=O)C>[CH:14]1([CH2:13][O:3][C:4]2[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=2)[CH2:17][CH2:16][CH2:15]1

参加物

7

反応物 4

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2734658(Bromomethyl)cyclobutane

生成物 1

HCID 654582914-(Cyclobutylmethoxy)benzaldehyde収率 76.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of sodium hydride (60% dispersion in mineral oil, 0.328 g) in N,N-dimethylformamide (15.0 mL), a solution of 4-hydroxybenzaldehyde (1.00 g) in N,N-dimethylformamide (5.00 mL) was added at 0° C. and thereafter the mixture was stirred at room temperature for 30 minutes. After adding (bromomethyl)cyclobutane (1.22 g), the mixture was stirred at 70° C. for 24 hours. After cooling the reaction mixture to room temperature, 0.5 mol/L hydrochloric acid was added under cooling with ice and three extractions were conducted with ethyl acetate. The combined organic layers were passed through a phase separator and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-40:60) to give the titled compound as a colorless oil (1.19 g).

後処理

  1. stirringthe mixture was stirred at 70° C. for 24 hours
  2. temperatureAfter cooling the reaction mixture to room temperature
  3. temperatureunder cooling with ice and three extractions
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-40:60)

出典と根拠

ORDレコード
ord-793f93a6b864458891ae36d53bd1b4f9
出典データセット
uspto-grants-2016_08
特許番号
US09422240B2

反応ノート

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