Methane, dichloromethoxy- → 6-(4-Tert-butyl-cyclohexyloxy)-8-methyl-naphthalene-2-carbaldehyde

HRID 2404199노트

반응식

HRID 2404199 반응식
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]([CH3:22])[C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Sn](Cl)(Cl)(Cl)Cl.[CH3:28][O:29]C(Cl)Cl>ClCCCl.ClCCl>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([O:11][C:12]2[CH:21]=[C:20]3[C:15](=[C:14]([CH3:22])[CH:13]=2)[CH:16]=[C:17]([CH:28]=[O:29])[CH:18]=[CH:19]3)[CH2:9][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachlorideHCID 681727973-(4-Tert-butyl-cyclohexyloxy)-1-methyl-naphthalene

생성물 1

HCID 866684296-(4-Tert-butyl-cyclohexyloxy)-8-methyl-naphthalene-2-carbaldehyde수율 98.6%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a mixture of 3-(4-tert-butyl-cyclohexyloxy)-1-methyl-naphthalene (450 mg, 1.5 mmol) in 1,2-dichloroethane (9 mL) was added tin tetrachloride (236 uL, 2 mmol) at 0° C. After stirred at 0° C. for 1 hr, dichloromethyl methyl ether (183 uL, 2 mmol) was added. The solution was stirred at 0° C. for 1 hr and then warmed to room temperature. The mixture was added ice water and stirred for 1 hr, then the dark solution was diluted with dichloromethane and washed with water. The organic phase was washed with sodium bicarbonate aqueous, and dried over MgSO4. The drying agent was filtered off and the solvent was concentrated to dryness to give dark solid product (0.48 g, yield: 97%). ESI-MS: 325.20 (M+H)+.

후처리

  1. stirringThe solution was stirred at 0° C. for 1 hr
  2. temperaturewarmed to room temperature
  3. stirringstirred for 1 hr
  4. washwashed with water
  5. washThe organic phase was washed with sodium bicarbonate aqueous
  6. dry with materialdried over MgSO4
  7. filtrationThe drying agent was filtered off
  8. concentrationthe solvent was concentrated to dryness

출처 및 근거

ORD 기록
ord-c4eff4b594a346c0a18c8160f707311f
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802659B2

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