Synthesis of phenyloxirane

Preparation of phenyloxirane

Preparation of phenyloxirane

Preparation of phenyloxirane

Styrene (30 g, 0.29 mole) is added to a solution of peroxybenzoic acid (42 g, 0.30 mole) in chloroform (500 ml), and the mixture is set aside at 0° for 24 hours, being repeatedly shaken during the first few hours. Completion of the oxidation can be determined by titration of an aliquot part of the chloroform solution. Then the benzoic acid formed and the small excess of peroxybenzoic acid are removed by repeated extraction with 10% sodium hydroxide solution, and the organic phase is washed with water until free from alkali and then dried over sodium sulfate. Fractional distillation affords styrene oxide (24-26 g, 70-75 %) as a colorless liquid, b.p. 101° C/40 mm.

Org. Syn., 8, 102 (1928)

IUPAC Name

2-phenyloxirane

InChI

InChI=1S/C8H8O/c1-2-4-7(5-3-1)8-6-9-8/h1-5,8H,6H2

InChI Key

AWMVMTVKBNGEAK-UHFFFAOYSA-N

Canonical SMILES

C1C(O1)C2=CC=CC=C2

MeSH Synonyms

phenyloxirane, styrene 7,8-oxide, styrene oxide, styrene oxide, (+-)-isomer, styrene oxide, (R)-isomer, styrene oxide, (S)-isomer

Depositor-Supplied Synonyms

Styrene oxide, 2-Phenyloxirane, Phenyloxirane, 1,2-Epoxyethylbenzene, Phenylethylene oxide, Epoxystyrene, 96-09-3, Styryl oxide, Styrene epoxide, 1-Phenyloxirane, Styrene 7,8-oxide, Phenethylene oxide, Oxirane, phenyl-, (Epoxyethyl)benzene, Phenyl oxirane, Epoxyethylbenzene, 1-Phenyl-1,2-epoxyethane, Benzene, (epoxyethyl)-, oxirane, 2-phenyl-, 1,2-Epoxy-1-phenylethane, STYRENE-7,8-OXIDE, alpha,beta-Epoxystyrene, Fenyloxiran, Styreneoxide, NCI-C54977, 2-phenyl-oxirane, (S)-Phenyloxirane, Epoxyethyl benzene, Fenyloxiran [Czech], NSC 637, (1,2-Epoxyethyl)benzene, .alpha.,.beta.-Epoxystyrene, Benzene, (1,2-epoxyethyl)-, CCRIS 1268, CHEBI:17907, HSDB 2646, AWMVMTVKBNGEAK-UHFFFAOYSA-N, EINECS 202-476-7, EP-182, BRN 0108582, AI3-18151, DSSTox_CID_1286, WLN: T3OTJ BR, DSSTox_RID_76058, DSSTox_GSID_21286, (R)-Styreneoxide, CAS-96-09-3, (R)-2-PHENYL-OXIRANE, (R)-(+)-Styrene-d5 Oxide, Styrene oxide-d8, Phenyloxirane, d8, 2-(phenyl)oxirane, (+)-styrene oxide, phenyl-ethylene oxide, (+/-)-styrene oxide, 1,2-epoxyethyl benzene, AC1L1OEJ, AC1Q1HFH, (.+/-.)-Styrene oxide, S5006_ALDRICH, (+/-)-phenylethylene oxide, SCHEMBL21026, (+-)-STYRENE OXIDE, BIDD:ER0688, W513504_ALDRICH, ACMC-20978q, NSC637, CHEMBL1605493, DTXSID2021286, Ethane, 1,2-epoxy-1-phenyl-, 77950_FLUKA, CTK3I6866, NSC-637, NSC7582, BB_NC-2270, NSC-7582, Tox21_202112, Tox21_300110, ANW-13656, AR-1I7152, BBL027496, MFCD00005121, STL146352, AKOS000120666, AKOS016843291, AC-9510, AC-9511, LS-2000, MCULE-4265681704, RP19371, TRA0022766, TRA0060537, VC30408, NCGC00091674-01, NCGC00091674-02, NCGC00091674-03, NCGC00253978-01, NCGC00259661-01, AK-84374, BP-21407, H390, HE028548, HE074026, KB-60632, SC-65236, DB-004092, TR-030115, A4520, E0013, FT-0605077, FT-0605345, C02083, 5-17-01-00577 (Beilstein Handbook Reference), I14-0017, J-503834, I14-22967, F0001-2287, 62497-63-6, 67253-49-0

Removed Synonyms

S-Phenyloxirane, (R)-Phenyloxirane, (S)-Styrene oxide, (R)-Styrene oxide, (R)-2-phenyloxirane, (R)-(Epoxyethyl)benzene, (S)-Phenylethylene oxide, C8H8O, (R)-(+)-Styrene oxide, styrene oxide, (R)-isomer, styrene oxide, (S)-isomer, styrene oxide, (+-)-isomer, Benzene, (epoxyethyl)-, (R)-, CID7276, MolPort-001-779-757, c0037, RTR-030115, C013690, 20780-53-4, 20780-54-5

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1 comment


  1. Post author
    chemikalien

    Alternativ kann man auch mit Wasserstoffperoxid und Acetonitril arbeiten.
    Edukte:
    0,5n NaOH 350ml
    2000 ml Methanol
    416 gr Styrol 4 mol
    206 gr Acetonitril 5 mol
    566 gr 35% Wasserstoffperoxid 4 mol
    50ml 0,1n di-Natriumhydrogenphosphat Berechnung 50ml x 14.195884 / 1000 =0.71gr
    Apparaturen
    5 Liter Doppelmantelkolben mit Kühler Thermometer Rührer Tropftrichter
    Rotovapor und Fraktionierkolonnen und Vakuumpumpe.
    Literatur:
    Thieze Eicher S 80 Org, Chem. Grundpraktikum
    Beilstein Beil. 17,V,1,577
    http://forum.lambdasyn.org/index.php/topic,1181.0.html

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