DR ANTHONY MELVIN CRASTO,WorldDrugTracker, helping millions, A 90 % paralysed man in action for you, I am suffering from transverse mylitis and bound to a wheel chair, With death on the horizon, nothing will not stop me except God................DR ANTHONY MELVIN CRASTO Ph.D ( ICT, Mumbai) , INDIA 25Yrs Exp. in the feld of Organic Chemistry,Working for GLENMARK GENERICS at Navi Mumbai, INDIA. Serving chemists around the world. Helping them with websites on Chemistry.Million hits on google, world acclamation from industry, academia, drug authorities for websites, blogs and educational contribution

Tuesday 12 August 2014

Ethyl-2-(4-chlorophenyl)cyclopropanecarboxylate

Ethyl-2-(4-chlorophenyl)cyclopropanecarboxylate



Figure US20020052370A1-20020502-C00171

A mixture of 4-chlorostyrene (10.1 ml, 96 mmol) and rhodium acetate dimer (1 g, 4.5 mmol) in toluene (50 ml) was heated to 85° C. before adding ethyl diazoacetate (11.3 mls, 94 mmol) over 30 mins and the whole then heated at 80° C. for a further 1 h before concentration in vacuo. The residue was then purified by column chromatography using 1:2 DCM:pentane as eluant to give the title product as a colourless oil (7.8 g, 37%); R1:2 (DCM:pentane) 0.35; 

1HNMR (400 MHz, CDCl3) δ 1.15-1.3 (m, 4H), 1.5-1.7 (m, 1H), 1.8-1.9 (m, 1H), 2.4-3.55 (m, 1H), 4.2 (q, 2H), 6.95 (d, 2H), 7.20-7.28 (m, 2H); and LRMS: m/z, M+NH4+242.

trans-2-(4-Chlorophenyl)cyclopropanecarboxylic acid
Figure US20020052370A1-20020502-C00172


The product from preparation 73 (7.8 g, 37 mmol) was dissolved in EtOH (75 mls) at room temperature under nitrogen and sodium methoxide (8.1 g, 150 mmol) was added portionwise over 15 mins. After the addition was complete, the mixture was then refluxed for 18 h. The reaction mixture was concentrated in vacuo, and the resulting residue diluted with DCM and water (150 mls, 2:1 mixture). The organic layer was removed, and the aqueous layer re-extracted with DCM (2×50 mls). The combined organic extracts were dried over MgSOand evaporated to provide the trans ester (4.96 g, 62%). Acidification of the aqueous layer with concentrated HCl to pH 1 resulted in a white precipitate, which was filtered and dried under vacuum to provide the hydrolysis product (the corresponding acid) as a white powder (1 .95 g, 27%). Dissolution of the ester in MeOH (50 mls), water (50 mls) and LiOH (1.34 g, 32 mmol) gave a clear solution which was heated at ca. 70° C. overnight. The reaction mixture was cooled, concentrated in vacuo, and acidified with concentrated HCl to pH 1. The resulting white precipitate was extracted with EtOAc (3×50 mls) and the combined organic extracts were dried over MgSOand evaporated to dryness, to provide the acid (4 g, 96%). This acid was combined with the hydrolysed product from the previous step to give a total of 5.95 g; 

1HNMR (400 MHz, CDCl3) δ 1.3-1.4 (m, 1H), 1.6-1.7 (m, 1H), 1.8-1.9 (m, 1H), 2.5-2.6 (m, 1H), 7.00 (d, 2H), 7.26 (d, 2H); LRMS: m/z, M-H 195.










DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO .....FOR BLOG HOME CLICK HERE

Join me on Linkedin

View Anthony Melvin Crasto Ph.D's profile on LinkedIn

Join me on Facebook FACEBOOK
Join me on twitterFollow amcrasto on Twitter     
Join me on google plus Googleplus

 amcrasto@gmail.com




Khajuraho Group of Monuments is located in India
Khajuraho Group of Monuments
Location of Khajuraho Group of Monuments in India.

Location in Madhya PradeshLocation in Madhya Pradesh

  1. Khajuraho Group of Monuments - Wikipedia, the free ...

    en.wikipedia.org/wiki/Khajuraho_Group_of_Monuments

    The Khajuraho Group of Monuments are a group of Hindu and Jain temples in Madhya Pradesh, India. About 620 kilometres (385 mi) southeast of New Delhi, ...























Hotel Chandela - A Taj Leisure Hotel








No comments:

Post a Comment