Water → 1-Chloro-1,2,3,4-tetrahydronaphthalene

HRID 2228461

반응식

HRID 2228461 반응식
[CH:1]1(O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.O.S(Cl)([Cl:21])=O>C(OCC)C.[Cl-].[Na+].O>[Cl:21][CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 962WaterHCID 1049PyridineHCID 107231,2,3,4-Tetrahydro-1-naphthalenolHCID 24386Thionyl Chloride

생성물 1

HCID 1887171-Chloro-1,2,3,4-tetrahydronaphthalene수율 96.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 57417360Sodium chloride; water용매

실험 절차

A 1 liter 3-necked flask equipped with a condenser, electronic thermocouple, mechanical stirrer and under a nitrogen atmosphere was charged with 1,2,3,4-tetrahydro-1-naphthol (34.3 g; 0.23 mol) in dry diethyl ether (420 ml). Pyridine (4.7 ml) was added and the flask was cooled to 16° C. in a bath of water and ice. A solution of thionyl chloride (50.7 ml; 0.70 mol) in ether (140 ml) was then added dropwise in 25 minutes and stirring continued overnight while allowing the bath to warm to ambient temperature. The reaction mixture was then poured into cold brine (400 g ice and 800 ml brine) and the organic phase was separated. The aqueous phase was extracted with diethyl ether (2×150 ml) and the combined organic extract was dried with sodium sulphate. Filtration and removal of solvent in vacuo gave 1,2,3,4-tetrahydro-1-chloronaphthalene (36.9 g) as an oil. This material was used without further purification.

후처리

  1. customA 1 liter 3-necked flask equipped with a condenser
  2. customthe organic phase was separated
  3. extractionThe aqueous phase was extracted with diethyl ether (2×150 ml)
  4. extractionthe combined organic extract
  5. dry with materialwas dried with sodium sulphate
  6. filtrationFiltration and removal of solvent in vacuo

출처 및 근거

ORD 기록
ord-2efb7c05105549c1b9d0e8ecc40e2cde
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06417183B1

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