Formaldehyde → Ethyl 4-(4-hydroxy-3-oxobutyl)benzoate

HRID 1656564ノート

反応式

HRID 1656564 の反応式
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH:14]=[O:15])=[CH:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2].[CH2:16]=[O:17].[Br-].C(C1SC2C=CC=CC=2[NH+]=1)C.C(N(CC)CC)C>C(O)C>[OH:17][CH2:16][C:14](=[O:15])[CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])=[CH:7][CH:8]=1

参加物

6

反応物 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 2757377Ethyl 4-(3-oxopropyl)benzoateHCID 68772949Ethyl benzothiazolium bromide

生成物 1

HCID 10609833Ethyl 4-(4-hydroxy-3-oxobutyl)benzoate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 1.1 g (5 mmol) of 3-(4-carbethoxyphenyl)propanal and 150 mg (5 mmol) of paraformaldehyde in 10 mL of ethanol, together with 230 mg (0.9 mmol) of ethyl benzothiazolium bromide and 90 mg (0.9 mmol) of triethylamine, is heated at about 70° C. for 16 hours. The reaction mixture is concentrated in vacuo and the product further purified by chromatography on silica gel, eluting with 15:85 ethyl acetate:hexane, to yield ethyl 4-(4-hydroxy-3-oxobutyl)benzoate as a colorless oil which solidifies upon standing; m.p. 51°-52° C. Anal. calcd for C13H16O4 : C, 66.09; H 6.83. Found: C, 66.29; H, 6.70.

後処理

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe product further purified by chromatography on silica gel
  3. washeluting with 15:85 ethyl acetate

出典と根拠

ORDレコード
ord-b84a1bc7fcda459b8fc671faf878f9be
出典データセット
uspto-grants-1993_10
特許番号
US05254687

反応ノート

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