Water → 1-Chloro-1,2,3,4-tetrahydronaphthalene
Reaction equation
[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]1Participants
Procedure
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.
Workup
- customA 1 liter 3-necked flask equipped with a condenser
- customthe organic phase was separated
- extractionThe aqueous phase was extracted with diethyl ether (2×150 ml)
- extractionthe combined organic extract
- dry with materialwas dried with sodium sulphate
- filtrationFiltration and removal of solvent in vacuo
Sources & evidence
- ORD record
- ord-2efb7c05105549c1b9d0e8ecc40e2cde
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06417183B1
Reaction notes
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