Synthesis of cis-stilbene

Preparation of cis-stilbene ((z)-stilbene; isostilbene; cis-1,2-diphenylethylene; (z)-1,2-diphenylethene)

Preparation of cis-stilbene (cis-stilbene; (z)-stilbene; isostilbene; cis-1,2-diphenylethylene; (z)-1,2-diphenylethene)

Preparation of cis-stilbene ((z)-stilbene; isostilbene; cis-1,2-diphenylethylene; (z)-1,2-diphenylethene)

9.5 g of diphenylacetylene is mixed under nitrogen with 17 g of diisobutylaluminium hydride and warmed at 45-50° C for 12 hours. The red product was then cooled in ice, treated cautiously with methanol and diluted sulfuric acid, and extracted with ether. The extract was washed with water and sodium hydrogen carbonate solution, dried over calcium chloride, and evaporated, yielding a residue whence distillation in a vacuum at 82-84 °C/0.4 mm or 147-148°/15 mm affords 7 g or 73% of cis-stilbene.

G. Wilke; H. Miiller, Chem. Ber., 89, 444 (1956);
A. E. G. Miller, J. W. Biss; L. H. Schwartzman, J. Org. Chem., 24, 627 (1959);
W. J. Gensler; J. J. Bruno, J. Org. Chem., 28, 1254 (1963);

IUPAC Name

(Z)-stilbene

InChI

InChI=1S/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11-

InChI Key

PJANXHGTPQOBST-QXMHVHEDSA-N

Canonical SMILES

C1=CC=C(C=C1)C=CC2=CC=CC=C2

Isomeric SMILES

C1=CC=C(C=C1)/C=C\C2=CC=CC=C2

Depositor-Supplied Synonyms

cis-Stilbene, (Z)-Stilbene, Isostilbene, cis-1,2-Diphenylethylene, (Z)-1,2-Diphenylethene, 645-49-8, cis-Diphenylethene, Stilbene, (Z)-, [(Z)-2-Phenylethenyl]benzene, 1,cis-2-Diphenylethene, 1,cis-2-Diphenylethylene, (Z)-1,2-Diphenylethylene, UNII-TTG5048Y3K, CCRIS 5932, CHEBI:36008, HSDB 4270, Benzene, 1,1′-(1,2-ethenediyl)bis-, (Z)-, PJANXHGTPQOBST-QXMHVHEDSA-N, EINECS 211-445-7, NSC 66424, 1,1′-(Z)-ethene-1,2-diyldibenzene, Benzene, 1,1′-(1Z)-1,2-ethenediylbis-, [Z]-1,2-diphenylethene, Z-stilbene, Dibenzal (cis), 103-30-0, cis-1,2-Diphenylethene, AC1NS9PI, DSSTox_CID_6049, S4808_ALDRICH, DSSTox_RID_77994, Ambap645-49-8, DSSTox_GSID_26049, MLS001050167, Stilbene, (Z)- (8CI), 1,2-Diphenylethene, (Z)-, ((1Z)-2-phenylvinyl)benzene, CHEMBL393702, TTG5048Y3K, [(Z)-2-Phenylethenyl]benzene #, MolPort-001-781-720, NSC66424, Tox21_200350, 9885AB, NSC-66424, NSC126882, AKOS016010738, LS-1551, NSC-126882, (Z)-(1,2-ethenediyl)-1,1-bisbenzene, (Z)-1,1′-(1,2-ethenediyl)bisbenzene, NCGC00091103-01, NCGC00091103-02, NCGC00257904-01, AJ-57688, AK115882, CAS-645-49-8, SMR001216580, 1,1′-(1,2-Ethanediyl)bis[benzene], cis, 1,1′-[(1Z)-ethene-1,2-diyl]dibenzene, Benzene,1′-(1,2-ethenediyl)bis-, (Z)-, DB-054687, KB-212075, TL8004590, FT-0623948, S0089, ST24026683, ST45022236, (1,2-Ethenediyl)-1,1′-bisbenzene, (Z)-, Benzene, 1,1′-(1,2-ethenedyl)bis-, (Z)-, A800711, A834808, 3B3-002676, Benzene, 1,1′-(1,2-ethenediyl)bis-, (Z)- (9CI), UNII-W1WNW14Z2I component PJANXHGTPQOBST-QXMHVHEDSA-N

Removed Synonyms

Benzyl butyl ether, CID5356785

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