3-Acetylphenanthrene → 3-Phenanthrenecarboxylic acid

HRID 1383036Notes

Reaction equation

HRID 1383036 reaction equation
[CH:1]1[C:14]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH:15]=[O:16].C(C1C=CC2C3C(=CC=CC=3)C=CC=2C=1)(=[O:19])C.C(C1C=CC2C=CC3C(C=2C=1)=CC=CC=3)(=O)C>>[CH:4]1[C:5]2[CH:6]=[CH:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]=2[CH:1]=[C:2]([C:15]([OH:16])=[O:19])[CH:3]=1

Participants

4

Reactant 3

HCID 748673-AcetylphenanthreneHCID 80060Methyl 2-phenanthryl ketoneHCID 3015327Phenanthrene-2-carbaldehyde

Product 1

HCID 240563-Phenanthrenecarboxylic acidYield 51%

Procedure

Using the procedure outlined in 2A for 2-acetylphenanthrene, 3-acetylphenanthrene (Aldrich, technical grade), 25 g, 0.114 mol) gave 13 g (51%) of phenanthrene-3-carboxylic acid. 15.6 g (0.07 mol) of this acid was converted to the corresponding acid chloride, then to 8.37 g (58%) of phenanthrene-3-carboxaldehyde mp 78°-80° (lit. 79.5°-80°, E. Mosettig and J. van de Kamp, J. Amer. Chem. Soc. 55 2395 (1933)), (C, H).

Sources & evidence

ORD record
ord-51e3744d5edb47bb947311dfaff957f1
Source dataset
uspto-grants-1989_02
Patent number
US04808625

Reaction notes

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