Monobenzone → ((p-(Benzyloxy)phenoxy)methyl)oxirane

HRID 2066617Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:17][CH:18]1[CH2:20][O:19]1>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:17][CH:18]2[CH2:20][O:19]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 7638Monobenzone

HCID 18430Epibromohydrin

Product 1

HCID 119882((p-(Benzyloxy)phenoxy)methyl)oxiraneYield 79%

Procedure

Alkylation of 4-(benzyloxy)phenol with 2-(bromomethyl)oxirane (76) as in Example 2A, followed by chromatography of the product on silica gel, eluting with 0-25% CH2Cl2/petroleum ether (foreruns) and then with 25% CH2Cl2/petroleum ether, gave 2-{[4-(benzyloxy)phenoxy]methyl}oxirane (78) (reported by Kopka et al., 2003 using epichlorohydrin) (79%) as a white solid: mp (CH2Cl2/pentane) 61-62° C.; 1H NMR (CDCl3) δ 7.44-7.28 (m, 5H), 6.90 (dt, J=9.3, 2.8 Hz, 2H), 6.85 (dt, J=9.3, 2.8 Hz, 2H), 4.16 (dd, J=11.1, 3.3 Hz, 1H), 3.92 (dd, J=11.1, 5.6 Hz, 1H), 3.32 (m, 1H), 2.89 (dd, J=4.8, 4.3 Hz, 1H), 2.73 (dd, J=5.0, 2.7 Hz, 1H).

Workup

washeluting with 0-25% CH2Cl2/petroleum ether (foreruns)

Sources & evidence

ORD record: ord-062e7c9d476e49b286979e8dcfca47f5
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293734B2

Reaction notes

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