Styrene → Styrene Oxide

HRID 1684880Notes

Reaction equation

[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC1(C)O[C@H]2[C@@H]3OC(C)(C)O[C@]3(C(O)=O)O[C@H]2C[O:11]1.O.OO.NC(N)=O>ClCCl>[C:3]1([CH:2]2[CH2:1][O:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Styrene (1 g, 9.6 mmol) was taken with 100 mg Immobilized lipase and 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid monohydrate (0.3 g, 1.03 mmol) in dry dichloromethane (15 mL) and stirred at 25° C. and added urea hydrogen peroxide (3 g, 32 mmol) portion-wise at a pH 5 for 20 hours. The reaction was monitored occasionally on TLC. The mixture was filtered and washed the residue with dichloromethane and the filtrate was reduced its volume under reduced pressure using vacuum flash evaporator. The product was purified by preparative TLC with 40% CH2Cl2/hexane. Yield: 70%; oil (Found: C, 79.91; H, 6.65. C8H8O requires C, 79.97; H, 6.71%); Rf (40% CH2Cl2/hexane) 0.55. The enantiomeric excess was determined by HPLC analysis using a Chiralcel OD column [iPrOH:hexane=0.2:99.8, flow rate 0.2 cm3 min−1], [α]D22+21.6 (c 0.7, PhH) 48% ee; {lit., [α]D22+44.8 (c 1.00, PhH), R}; νmax (neat/cm−1) 1496, 1476, 1452, 1390; δH (300 MHz; CDCl3) 2.80 (1H, dd, J 2.6 and 5.5, HCOCHH), 3.13 (1H, dd, J 4.1 and 5.5, HCOCHH), 3.85 (1H, dd, J 2.6 and 4.0, PhCHOCH2), 7.26-7.36 (5H, m, 5×CH, arom.); δC (300 MHz; CDCl3) 51.7 (CH2), 52.8 (CH), 125.9, 126.3, 128.6, 128.9 and 138.0 (6×C-Ph). MS m/z (rel. intensity %): 122 (M+2, 15), 121 (M+1, 43), 120 (M+, 20), 105(100), 91(68), 77 (88).

Workup

filtrationThe mixture was filtered
washwashed the residue with dichloromethane
customvacuum flash evaporator
customThe product was purified by preparative TLC with 40% CH2Cl2/hexane

Sources & evidence

ORD record: ord-dd416c6f9832432585d061103cf4b2ef
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148118B2

Reaction notes

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