6-allyloxy-indan-1-one

http://www.google.com/patents/US8242291

alkylation of the hydroxyl of 6-hydroxy-indanone, (II), to obtain 6-allyloxy-indan-1-one, (III):

EXAMPLE 1

This example refers to reaction a of the process of the invention.

20 kg of 6-hydroxy-indanone are suspended in 120 l of acetone, and 29.9 kg of potassium carbonate and 19.7 kg of allyl bromide are added. The reaction mixture is heated to reflux and checked after 15 h (TLC). It is cooled to 20-25° C. and filtered, washing the filtered solid with 40 l of acetone. The filtered solution is concentrated to dryness at reduced pressure. The oil obtained is recovered with 25 l of heptane and re-concentrated to dryness obtaining a solid (25.9 kg). The thus obtained solid is dissolved at 60° C. in 125 l of heptane, and is then cooled to 0° C. for at least one hour. It is filtered and washed with 25 l of cold heptane. 22.3 kg of intermediate (III) are obtained in a pale yellow solid form of quality suitable for continuation of the synthesis.

An ¹H-NMR (500 MHz, CDCl₃) spectroscopic analysis is performed on part of the product thus obtained, purified by chromatography for analytical purposes (silica gel, heptane 8-ethyl acetate 2), obtaining the following result:

2.74 ppm, t J=6 Hz, 2H, AR C=0 CH2CH2 AR

3.10 ppm, t, J=6 HZ, 2H, AR C=0 CH2CH2 AR

4.60 ppm, broad d, J=5 Hz, 2H, 0-CH2CH=CH2

5.32 ppm, dd, J=10 Hz, 1H, 0-CH2CH=CH2

5.45 ppm, broad dd, J=16 Hz, 1H, 0-CH2CH=CH2

6.02-6.13 ppm, m, 1H; 0-CH2CH=CH2

7.20-7.27 ppm, m, 2H, 

7.40 ppm, d, J=8 Hz, 1H.

Industriale Chimica S.R.L.

INDUSTRIAL CHEMICAL SRL

Via Grieg, 13 - 21047 - SARONNO ( VA )

Tel .:		02 96426411th
Fax:		02 the 9,621,997th
VAT:		07462480158
Cod. Tax:		07462480158
Web:

Group:

Chemical, Pharmaceutical and Leather Chemical Pharmaceutical

Production sector:

PRODUCTION DEVELOPMENT RESEARCH CHEMICALS PHARMACEUTICALS

Products:

ACTIVE CHEMICAL PHARMACEUTICAL INDUSTRY

Brands:

Export Markets:

SWITZERLAND SPAIN

Inglese:  Product activity:  Products:

Company Profile:

Industrial Chemistry Srl company active in Saronno since 1984, has experienced a rapid and continuous expansion going from 21 employees to more than 60 current '94. It is a group company Chemo that, by holding well 45 international patents, produces synthetic active ingredients for the preparation of many types medicines including anti-inflammatory, anti-ischemic, diuretics and steroids. As evidence of the very high quality of the productions the company markets its products are almost exclusively foreign. Industrial Chemistry also invests every year a good proportion of turnover in research. Since 1988 the company has entered in the register of highly qualified laboratories, authorized to conduct applied research in favor of small and medium industries, prepared by the Ministry of Scientific Research. In company are rigorously applied standard operating procedures for all production activities that ensure the highest level of safety for the operators and the environment. Street View Via Edvard Hagerup Grieg, 13 21047 Saronno VA, Italy