INDANE COMPOUNDS, PROCESSES OF MAKING SAME AND THEIR USE AS FRAGRANCE MATERIAL

摘要

1300970 Indane compounds and their use as fragrance materials INTERNATIONAL FLAVOURS & FRAGRANCES Inc 4 Aug 1970 [18 Aug 1969 (5)] 37592/70 Heading C2C [Also in Divisions A5 and C5] The invention comprises indane compounds of formula in which formulµ one of R 1 and R 2 is 0 and the other is hydrogen; R 6 is hydrogen, alkyl or an acyl group and R 3 is a carbonyl oxygen or a hydroxy, acyloxy or alkoxy group. The compounds of Formula I also include their 7,7aepoxy derivatives. These compounds may be prepared by (a) oxidizing atetrahydro-1,1,2,3,3- pentamethylindane with a hexavalent chromium oxidizing agent, (b) by reacting a 3a,7a-epoxyhexahydro - 1,1,2,3,3 - pentamethylindane with a trialkoxyaluminium, (c) by oxidizing a tetrahydro-1,1,2,3,3-pentamethylindane with a percarboxylic acid and obtaining a 3d,7d-epoxyhexahydropentamethylindane, (d) by treating 4d,7d - epoxyhexahydro - 1,1,2,3,3 - pentamethylindane with a strong protonic acid to form 4,5-dihydropentamethylindane, (e) by oxidizing a 1,1,2,3,3-pentamethylhexahydroindanol with a hexavalent chromium oxidizing agent to provide the corresponding ketone. The following compounds are prepared in the examples: 4,5,6,7 - tetrahydro - 1,1,2,3,3 - pentamethylindane; 6,7 - dihydro - 1,1,2,3,3 - pentamethyl-4(5H)-indanone; 7,7a-epoxy-5,6,7,7atetrahydro - 1,1,2,3,3 - pentamethyl - 4(3aH)- indanone; 5 - methoxy - 1,1,2,3,3 - pentamethylindane; 6,7 - dihydro - 1,1,2,3,3 - pentamethyl - 5(4H) - indanone and 7,7a - dihydro- 1,1,2,3,3 - pentamethyl - 5(6H) - indanone; 3a,7a - epoxyhexahydro - 1,1,2,3,3 - pentamethylindane; 4,5,6,7 - tetrahydro - 1,1,2,3,3- pentamethyl - 4 - indanol; methyl - 4,5,6,7- tetrahydro - 1,1,2,3,3 - pentamethyl - 4 - indanyl ether; 4,5,6,7 - tetrahydro - 1,1,2,3,3 - pentamethyl - 4 - indanyl acetate; 4,5 - dihydro- 1,1,2,3,3 - pentamethylindane; 1,1,2,3,3 - pentamethylhexahydroindan-5-ol and 1,1,2,3, 3-pentamethylhexahydroindan-4-ol. The compounds of the invention are reported to have a woody odour and may be incorporated as fragrances in soaps, solid, liquid detergents and cosmetics.