6065. 5,5′-Methylenedisalicylic Acid

Nomenclature

CAS number: 122-25-8
3,3′-Methylenebis[6-hydroxybenzoic acid]; 4,4′-dihydroxydiphenylmethane-3,3′-dicarboxylic acid.
C15H12O6; mol wt 288.25.
C 62.50%, H 4.20%, O 33.30%.

Description and references

Prepd from salicylic acid and formaldehyde in the presence of sulfuric acid: Clemmensen, Heitman, J. Am. Chem. Soc. 33, 737 (1911).

Chemical structure

Properties

Wedge-like cryst from acetone + benzene. Bitter taste. Dec 238° (higher-melting material may be impure). Turns red at 180° and starts giving off CO2. Freely sol in methanol, ethanol, ether, acetone, glacial acetic acid. Very slightly sol in hot water. Practically insol in benzene, chloroform, carbon disulfide, petr ether.

Derivative

Bacitracin salt see Bacitracin Methylenedisalicylate.

Derivative

Diacetyl deriv.
C15H10O6(CH3CO)2; mol wt 372.33.
C 61.29%, H 4.33%, O 34.38%.

Properties

White powder, mp 142°, practically insol in water, sol in acetone, ethanol.