Formaldehyde → Benzoic acid, 3-methoxy-, chloromethyl ester

HRID 1496793노트

반응식

HRID 1496793 반응식
[C:1]([OH:11])(=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.S(Cl)(Cl)=O.[C:16]([Cl:26])(=O)C1C=CC=C(OC)C=1.C=O>[Cl-].[Zn+2].[Cl-]>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:1]([O:11][CH2:16][Cl:26])=[O:10]

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 114613-Methoxybenzoic AcidHCID 24386Thionyl ChlorideHCID 74374m-Anisoyl chloride

생성물 1

HCID 12009022Benzoic acid, 3-methoxy-, chloromethyl ester수율 26%

시약·촉매·용매 1

HCID 3007855Zincchloride촉매

반응 조건

온도
80 °C

실험 절차

A similar procedure (Lu, M. C. et al. J. Med. Chem. 1987, 30, 273-278 and Iyer, R. P. et al. Synth. Commun. 1995, 25, 2739-2749) to that described for the preparation of 50 was followed using m-anisic acid (4.1 g, 26.9 mmol) and thionyl chloride (4 mL), under reflux for 1 h. A mixture of crude m-anisoyl chloride, paraformaldehyde (808 mg, 26.9 mmol) and zinc chloride (28 mg, 0.21 mmol) was then stirred at 80° C. for 16 h. Purification by flash chromatography (hexane/ethyl acetate 19:1) afforded chloromethyl m-methoxybenzoate (47) as a pale green oil (1.4 g, 6.86 mmol, 26%). 1H NMR 3.86 (3H, s, OMe), 5.95 (2H, s, CH2), 7.14-7.17 (1H, m, Ar), 7.36-7.40 (1H, m, Ar), 7.58-7.59 (1H, m, Ar), 7.66-7.69 (1H, m, Ar).

후처리

  1. temperatureunder reflux for 1 h
  2. customPurification by flash chromatography (hexane/ethyl acetate 19:1)

출처 및 근거

ORD 기록
ord-89260c74591d47e0aae496e348ab07b9
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09198420B2

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