Water → (4-Hydroxyphenyl)(4-iodophenyl)methanone

HRID 229229Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].O>C1C=CC=CC=1>[OH:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=2)=[O:9])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of (4-Iodophenyl)[4-(methyloxy)phenyl]methanone (142) (1.50 g, 4.44 mmol) and AlCl3 (2.40 g, 17.74 mmol) were refluxed in benzene (50 mL) for 1.5 h and then cooled to 0° C. in an ice bath. Water (50 mL) was added slowly, and the mixture was extracted with ether (2×100 mL). The combined ethereal extracts were washed with water, brine, and dried over Na2SO4. Concentration and trituration with hot hexanes afforded 1.36 g (95%) of the title compound as light brown solid. 1H NMR (400 MHz, CDCl3): δ 5.37 (br s, 1H), 6.90 (d, J=8.6 Hz, 2H), 7.47 (d, J=8.4 Hz, 2H), 7.75 (d, J=8.6 Hz, 2H), 7.83 (d, J=8.5 Hz, 2H). LCMS (ESI): m/z, 325 (M+H)+, 323 (M−H)−.

Workup

extractionthe mixture was extracted with ether (2×100 mL)
washThe combined ethereal extracts were washed with water, brine
dry with materialdried over Na2SO4
concentrationConcentration and trituration with hot hexanes

Sources & evidence

ORD record: ord-26eafe2fcde64f17960f3fdac3bb372f
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560589B2

Reaction notes

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