Synthesis of 9,10-dihydrophenanthrene-9-carboxylic acid

Preparation of 9,10-dihydrophenanthrene-9-carboxylic acid

Preparation of 9,10-dihydrophenanthrene-9-carboxylic acid

Preparation of 9,10-dihydrophenanthrene-9-carboxylic acid

5.69 g of phenanthrene-9-carboxylic acid, 1 g of sodium amide, and 90 ml of liquid ammonia are placed in a reaction vessel fitted with a reflux condenser that can be cooled to —70° C by alcohol-dry ice and with a magnetic stirrer. The mixture is stirred (around 4 hours) until the sodium amide is wholly dissolved and thereafter freshly cut, small pieces 1.2 g of sodium are added during 1 hour. The dark red mixture is stirred for a further 1.5 hour and then slowly decolorized by 10 ml ethanol. The ammonia is then allowed to evaporate, the residue dissolved in water and acidified with hydrochloric acid, and the thick brown oil is extracted in ether (two 25-ml portions). The combined extracts are washed with water, dried over anhydrous sodium sulfate, and treated with Norite. Evaporation of the ether yields the 9,10-dihydrophenanthrene-9-carboxylic acid, with melting point 122-124° C.

H. de Koning et aL, Rec Trav. Chim., 83, 364 (1964)

IUPAC Name

9,10-dihydrophenanthrene-9-carboxylic acid

InChI

InChI=1S/C15H12O2/c16-15(17)14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-8,14H,9H2,(H,16,17)

InChI Key

MOXWGTRDIRKZTH-UHFFFAOYSA-N

Canonical SMILES

C1C(C2=CC=CC=C2C3=CC=CC=C31)C(=O)O

Depositor-Supplied Synonyms

9,10-dihydrophenanthrene-9-carboxylic acid, 2222-30-2, NSC134500, AC1L5UUA, AC1Q5UNR, CTK1A6208, AR-1H5225, AKOS022655148, NSC-134500, 9-Phenanthrenecarboxylicacid, 9,10-dihydro-

Removed Synonyms

CID281641, 22334-99-2

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