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

HRID 1656564노트

반응식

HRID 1656564 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b84a1bc7fcda459b8fc671faf878f9be
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05254687

반응 노트

불러오는 중…