Hydrochloric Acid → 5-(Chloromethyl)-6-methylbenzo[d][1,3]dioxole

HRID 250219

반응식

HRID 250219 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1.C=O.Cl[CH2:14][Cl:15].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC>[Cl:15][CH2:14][C:10]1[C:2]([CH3:1])=[CH:3][C:4]2[O:8][CH2:7][O:6][C:5]=2[CH:9]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 6344DichloromethaneHCID 815641,3-Benzodioxole, 5-methyl-

생성물 1

HCID 105594165-(Chloromethyl)-6-methylbenzo[d][1,3]dioxole수율 62%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 3283Diethyl Ether용매

반응 조건

온도
0 °C

실험 절차

At about 0° C., 5-methylbenzo[d][1,3]dioxole (500 mg, 3.68 mmol) and formaldehyde (37% in water, 0.7 mL) were sequentially added to a mixture of dichloromethane (6.8 mL), tetrabutylammonium bromide (80 mg) and concentrated hydrochloric acid (6.5 mL). Under continuous stirring, the mixture was maintained at about 0° C. for about 1 hour and then at ambient temperature for about 4 hours. The mixture was diluted with ether (100 mL). After standard extractive workup, the resulting solid residue was heated with hexanes (100 mL) and the insolubles were removed by filtration. The filtrate was concentrated to give desired product (420 mg, 62%). 1H NMR (300 MHz, CDCl3) δ 6.89 (s, 1H), 6.69 (s, 1H), 5.94 (s, 3H), 4.56 (s, 2H), 2.35 (s, 3H); GC-MS: m/z=184 (MH)+.

후처리

  1. customthe insolubles were removed by filtration
  2. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-b6b6d050f2924effa5aa7dbff1654bc5
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863308B2

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