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Properties of substance:

salol



skc-file

Synonyms:

phenyl salicylate
2-hydroxybenzoic acid phenyl ester

Group of substances:

organic

Physical appearance:

colorless rhombic crystals

Empirical formula (Hill's system for organic substances):

C13H10O3

Structural formula as text:

HOC6H4COOC6H5

Molar/atomic mass: 214.217

Melting point (°C):

41.82

Decomposition temperature (°C):

280

CAS №: 118-55-8


Solubility (g/100 g of solvent):

acetic acid 99,5%: 172 (21.5°C) [Ref.]
acetone: 1010 (30°C) [Ref.]
amyl acetate: 580 (30°C) [Ref.]
amyl alcohol: 25.7 (25°C) [Ref.]
benzene: 229 (25°C) [Ref.]
benzine: 90.8 (25°C) [Ref.]
carbon tetrachloride: 285 (25°C) [Ref.]
chloroform: very soluble [Ref.]
diethyl ether: very easily soluble [Ref.]
ethanol 80%: 8.34 (25°C) [Ref.]
ethanol 90%: 16.3 (25°C) [Ref.]
ethanol abs.: 53.8 (25°C) [Ref.]
ethyl acetate: 470 (25°C) [Ref.]
glycerol: very slightly soluble [Ref.]
methyl ethyl ketone: 620 (25°C) [Ref.]
oil of almonds: 27 [Ref.]
pyridine: 381 (20°C) [Ref.]
toluene: 510.5 (25°C) [Ref.]
water: 0.015 (25°C) [Ref.]
xylene: 678 (32.5°C) [Ref.]

Density:

1.2614 (30°C, g/cm3)
1.1553 (50°C, d4)

Synthesis 1:

Reference: Bader, A. R., Kontowicz, A. D. Phenyl Esters / Journal of the American Chemical Society. - 1953. - Vol. 75, No. 21 pp. 5417 [doi: 10.1021/ Ja01117a504]

50 g. (0.362 mol.) of salicylic acid, 150 g. (1.59 mol.; 4.4 eq.) of phenol and 100 g. of polyphosphoric acid were stirred and heated on the steam-bath for 24 hours. The cooled mixture was diluted with water, extracted with toluene; and the toluene solution was extracted with aqueous sodium bicarbonate solution from which 14 g. (28%) of unreacted salicylic acid was recovered on acidification. The toluene solution was washed, stripped in vacuo and the residue distilled to yield unreacted phenol and 53 g. (68%; 95% based on unrecovered salicylic acid) of phenyl salicylate, b.p. 108—110° at 0.4 mm., which crystallized in the receiver. There was no flask residue. One crystallization from methanol yielded 49 g. of pure product melting at 42—43°.

Vapour pressure (Torr):

12 (173°C)

References:

  1. CRC Handbook of Chemistry and Physics. - 95ed. - CRC Press, 2014. - pp. 3-458
  2. Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941. - pp. 723-724
  3. The Merck Index. - 15th ed. - Royal Society of Chemistry, 2013. - pp. 1358
  4. Yalkowsky S.H., Yan H. Handbook of aqueous solubility data. - CRC Press, 2003. - pp. 902
  5. Беликов В.Г. Учебное пособие по фармацевтической химии. - М.: Медицина, 1979. - pp. 174 [Russian]
  6. Краткая химическая энциклопедия. - Т. 4: Пирометаллургия-С. - М.: Советская энциклопедия, 1965. - pp. 736 [Russian]
  7. Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962. - pp. 1369, 1558-1559 [Russian]
  8. Справочник химика. - 2 изд., Т. 2. - Л.-М.: Химия, 1964. - pp. 938-939 [Russian]
  9. Хёрд Ч.Д. Пиролиз соединений углерода. - Л.-М.: ГОНТИ РКТП СССР, 1938. - pp. 432, 529 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru