Hydrochloric Acid → Fluoreneone

HRID 7333

Reaction equation

HRID 7333 reaction equation
C(O[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13](OCCCC)=[C:12](F)[CH:11]=2)=[CH:6][C:5]=1F)C.C([Li])CCC.[C:28](=[O:33])(OC)OC.Cl>CCCCCC.O1CCCC1>[C:28]1(=[O:33])[C:6]2[C:7]([C:10]3[C:11]([CH:5]=2)=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:8][CH:9]=[CH:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 120674464-Ethoxy-3,3'-difluoro-4'-butoxybiphenylHCID 178418339Butyllithium

Product 1

HCID 22281833Fluoreneone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

60 mmol of 4-ethoxy-3,3′-difluoro-4′-butoxybiphenyl (5) are introduced into 200 ml of tetrahydrofuran, and the mixture is cooled to −70° C. 120 mmol of a 1.6 M solution of n-butyllithium in hexane are added dropwise, and the mixture is stirred at this temperature for 2 hours. 60 mmol of dimethyl carbonate are subsequently added rapidly with vigorous stirring, the mixture is stirred at −70° C. for a further hour, allowed to warm to 0° C., hydrolysed with dilute hydrochloric acid and subjected to conventional work-up.

Workup

  1. stirringthe mixture is stirred at −70° C. for a further hour

Sources & evidence

ORD record
ord-d72ec14bcd7c4423a145eaa149263f3b
Source dataset
uspto-grants-2006_08
Patent number
US07087272B2

Linked notes

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