Hydrochloric Acid → Benzophenone

HRID 381810Notes

Reaction equation

O[C:2]1[C:11](C(O)=O)=[CH:10][C:9]2[C:4](=CC=CC=2)[C:3]=1[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)C=C(C(O)=O)C=1O.C1([Li])C=CC=CC=1.[OH2:36].Cl>O1CCCC1>[C:3]1([C:15]([C:24]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:36])[CH:4]=[CH:9][CH:10]=[CH:11][CH:2]=1

Participants

Conditions

Temperature: -78 °C

Procedure

With stirring under dry nitrogen, 2,2′-dihydroxy-1,1′-binaphthalene-3,3′-dicarboxylic acid (8.42 g, 22.5 mmol) was dissolved in dry tetrahydrofuran (500 mL) then cooled to −78° C. with a dry ice/acetone bath. Phenyllithium (100 mL of 1.8 M in 70/30 cyclohexane/ether, 0.18 mol) was added dropwise, then the solution was allowed to warm to ambient temperature. After stirring overnight, deionized water (50 mL) was slowly added to the reaction solution at 0° C. With vigorous stirring, 1 M hydrochloric acid was added dropwise until the water phase became strongly acidic (pH=2). The organic phase was washed with water in a separatory funnel, then dried over magnesium sulfate and evaporated. The orange residue was redissolved in dichloromethane and eluted through a silica gel plug. The orange filtrate was evaporated to yield 2,2′-dihydroxy-1,1′-binaphthalene-3,3′-bis (phenylketone) as a yellow solid (10.5 gm).

Workup

temperatureto warm to ambient temperature
stirringAfter stirring overnight
washThe organic phase was washed with water in a separatory funnel
dry with materialdried over magnesium sulfate
customevaporated
dissolutionThe orange residue was redissolved in dichloromethane
washeluted through a silica gel plug
customThe orange filtrate was evaporated

Sources & evidence

ORD record: ord-532cd9fe830e4928819605b5d695a32b
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06307107B1

Reaction notes

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