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

HRID 250219

反応式

HRID 250219 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-b6b6d050f2924effa5aa7dbff1654bc5
出典データセット
uspto-grants-2011_01
特許番号
US07863308B2

関連ノート

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