Preparation of 2-Aminobenzaldehyde
A Fragrant Component of Floral Odors
Brian D. Foy, R. Allen Smudde and William F. wood'
Humboidt State University, Arcata, CA 95521
2-Aminobenzaldehyde(1) has recently been identified as
an important component in the fragrant scents of many
flowers (Id).These flowers include broom (Spartium
junceum), false acacia (Robinia pseudoacacia), European
bird cherry (Padus auium), lily (Lilium candidum),
seringat (Philadelphus coronarius), Pittosporum tobira,
Hypecoum imberbe, and H. fragrant. This chemical is also
responsible for the "sweet" or fragrant odor of the wild
mushroom Hebeloma saccharialens (6).
2-Aminobenzaldehyde is prepared by reduction of 2-
nitrobenzaldehyde (2) with aqueous ferrous sulfate and
ammonia. Since the product contains both aldehyde and
amino groups it polymerizes easily. This means that it
must be isolated rapidly aRer it forms, which is done by
steam distillation of the product from the reaction mix-
ture. This experiment is modified for student usage from a
previously published procedure (7).
Experimental Procedure
2-Aminobenzaldehyde (1). To a 250-mL, two-necked,
round-bottomed flask is added 60 mL of water, 17.5 g
(0.063 mole) of ferrous sulfate heptahydrate, and 1.0 mL of
1M HCl. The flask is shaken until the ferrous sulfate dis-
solves. Then 1.0 g (0.0066 mole) of 2-nitrobenzaldehydefol-
lowed immediately by 10 mL of concentrated ammonium
322 Journal of Chemical Education
hydroxide is added to the flask. The resulting black precip-
itate is thoroughly mixed for a few seconds. Immediately,a
distillation condenser is fitted in the upper neck of the
flask and a thermometer immersed in the liquid from the
other neck of the flask. The flask is rapidly heated with a
flame until the temperature of the liquid is 80 -C and is
kept at this temperature for exactly 10 min. At this point,
the flask is rapidly heated to boiling, and 40 mL of distil-
late is collected in a flask immersed in an ice bath. The
product steam-distills with the water and forms crystals in
the receiver. The light-yellow crystals are collected by suc-
tion filtration in a Biichner funnel and dried by drawing
air through the funnel. The yield was 0.40g (50%).
The product has the following properties:
FT-IR (CCI,) 3502,3354,2828,2741,1673,1619,1481,1459,
1395, 1320,1204,1158,884, and 665 en-';
EI-MS, m/z = 121(Mt, 881, 93(100), 92(34), 84(12), 76(14),
66(92), 65(59), 63(12), 49(23), and 39(52);
NMR (CDC13),d = 116.01, 116.36, 118.81,135.20, 135.73,
149.90, and 194.09;
'H NMR (CDCI,), d = 6.14(broad, 2H), 6.64(d,lH), 6.74(t,lH),
7.31(t,lH), 7.48(d,lH), and 9.87(s,lH); and
mp = 34-36 'C (lit. 38-39 "C).
Literature Cited
~ ~ ~~ ~
1. Joulain, D. In Pmgnss in Eazatinl Oil R m o m h P d i n g s of the In&rnational
Symposium on Esspnfid Olk, (16th Meting. 1985). Brunke, E.J.. Ed.; Walter de
Gluyter:Berlin. 1986; pp 57-67.
2. JoulCn, D. FiavorFr~rBmncDJ 1987.2, 149-155.
3. Gmth, l:Bergstram, G;Pdlrnr, 0. Biochom. Syst. Eml. 1987,25,441&444.
4. Surbuw, H.; Guntert, M.: Schwane, B. J Ess Oil R e 1940,2,307316.
5. Dahl, A. E.: Wasagren,A. B.; Bewetram, C Biahom. Syst Em1 lssO,IS,157-168.
6. Wood, W F.; Bmwnson, M.; Srnudde, R. A.; and La-t, D. L. Mymlogin ism, 84,
935-PRR
~~~~-~
7. Smith, I. L;Opie, J. W In Organic Syntho~ps,CoN Val. 111,Homing E.C., Ed.: John
W k y :New Ymk, 1955; pp 5648.
'Correspondence may be addressed to this author.