Ethylene Oxide → 1,2-Bis(4-hydroxyphenyl)ethanone

HRID 1879241Notes

Reaction equation

C[C:2](C1C=C(Br)C(O)=C(Br)C=1)([C:4]1[CH:5]=[C:6](Br)[C:7]([OH:11])=[C:8](Br)[CH:9]=1)C.CC([C:26]1[CH:31]=[CH:30][C:29]([C:32]([OH:34])=O)=[CH:28][CH:27]=1)(C)C.[O:35]1CC1>>[OH:35][C:26]1[CH:27]=[CH:28][C:29]([C:32]([CH2:2][C:4]2[CH:9]=[CH:8][C:7]([OH:11])=[CH:6][CH:5]=2)=[O:34])=[CH:30][CH:31]=1

Participants

Reactant 3

HCID 6354Ethylene Oxide3×

HCID 6618Tetrabromobisphenol A

HCID 74034-tert-Butylbenzoic acid

Product 1

HCID 134272011,2-Bis(4-hydroxyphenyl)ethanone

Procedure

Synthesis of the diepoxide (diglycidyl ether) of 3,3′,5,5′-tetrabromobisphenol A (ETBBA) (See, Wang et al. J Appl Polym Sci 1991; 43: 1315-1321.) ETBBA was prepared in a similar manner as BEDB, using TBBA (24.9 g) instead of BHDB. This gave ETBBA (25.4 g, 85%). 1H-NMR (CDCl3, ppm): 7.30 (s, 4H, Ar—H), 4.21-4.18 (q, 2H, 2(—O—CH2-oxirane)), 4.09-4.05 (q, 2H, 2(—O—CH2-oxirane)), 3.51-3.46 (m, 2H, 2(oxirane CH2)), 2.92-2.90 (t, 2H, 2(oxirane CH2)), 2.75-2.74 (q, 2H, 2(oxirane CH2)), 1.60 (s, 6H, Ar—C(CH3)2—Ar).

Workup

customwas prepared in a similar manner as BEDB

Sources & evidence

ORD record: ord-658381879e774419adadb2b16551d4ab
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314202B2

Reaction notes

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