Chloromethyl Methyl Ether → Methyl 3-{[(methyloxy)methyl]oxy}benzoate

HRID 20622

반응식

HRID 20622 반응식
C(N(C(C)C)CC)(C)C.[CH3:10][O:11][CH2:12]Cl.[OH:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([O:20][CH3:21])=[O:19]>ClCCl>[CH3:10][O:11][CH2:12][O:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([O:20][CH3:21])=[O:19]

참가 물질

5

반응물 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 88068Methyl 3-Hydroxybenzoate

생성물 1

HCID 12955821Methyl 3-{[(methyloxy)methyl]oxy}benzoate수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

At about 0° C., diisopropylethylamine (1.7 g, 13.1 mmol) and methoxymethyl chloride (635 mg, 7.9 mmol) were sequentially added to a solution of methyl 3-hydroxybenzoate (1 g, 6.6 mmol) in dry dichloromethane (10 mL). The resulting mixture was maintained at ambient temperature for about 3 hours. Following standard extractive workup, the crude product was purified by flash column chromatography on silica gel (2×16 cm, petroleum ether/ethyl acetate=10/1 elution) to give the title product (1.03 g, 80%). 1H NMR (300 MHz, CDCl3) δ 7.71-7.69 (m, 2H), 7.36 (dd, 1H, J=7.8, 1.8 Hz), 7.25 (dd, 1H, J=7.8, 1.8 Hz), 5.22 (s, 2H), 3.92 (s, 3H), 3.50 (s, 3H); LC-MS: m/z=197 (MH)+.

후처리

  1. customthe crude product was purified by flash column chromatography on silica gel (2×16 cm, petroleum ether/ethyl acetate=10/1 elution)

출처 및 근거

ORD 기록
ord-8bc2e299758746c2868eeff47e513995
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745665B2

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