6-CHLOROHEXANAL synthesis

8synthesis methods

Product Name:6-CHLOROHEXANAL
CAS Number:52387-36-7
Molecular formula:C6H11ClO
Molecular Weight:134.6

2009-83-8 Synthesis

2009-83-8
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52387-36-7
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Yield: 94%

Reaction Conditions:

Stage #1:6-chloro-1-hexanol with oxalyl dichloride;dimethyl sulfoxide in dichloromethane at -78; for 0.666667 h;Inert atmosphere;
Stage #2: with triethylamine in dichloromethane;water at -78 - 20; for 0.5 h;Inert atmosphere;

Steps:

1 Preparation of 6-chlorohexanal (compound of formula IX, wherein A = -CHO)
A mixture of dimethyl sulfoxide (57.19g, 0.732mol) and methylene chloride (600mL) under nitrogen atmosphere was cooled to about -78°C and oxalyl chloride (55.74g, 0.439mol) was added drop wise at about the same temperature. The reaction mixture was stirred for about lOmin. A solution of 6-chlorohexanol (50g, 0.366mol) in methylene chloride (lOOmL) was slowly added to the reaction mixture at about -78°C. After completion of addition, the reaction mixture was stirred for about 30min and triethy] amine (148g, 1.464mol) was added drop wise at about -78°C. After completion of reaction, the temperature of the reaction mixture was raised to about room temperature and water (500mL) was added to the reaction mixture. The reaction mixture was stirred for about 30min and the two layers were separated. The organic layer was washed with 5% aqueous citric acid (400mL) and finally with water, dried over sodium sulphate and concentrated under vacuum at about 35°C to about 40°C to give 46.5g (94%) of 6- chlorohexanal as transparent oily mass.

References:

GLENMARK PHARMACEUTICALS LIMITED;GLENMARK GENERICS LIMITED;BHIRUD, Shekhar Bhaskar;SINGH, Sunil Kumar;NAIK, Samir;MISHRA, Sushanta;PATEKAR, Deepak Shantaram;KAJALE, Yogesh Baburao;PANDEY, Vipin WO2014/87428, 2014, A1 Location in patent:Paragraph 0144; 0152

19347-73-0 Synthesis