Hydrochloric Acid → 3,5-Dichloro-4-(4-chlorobenzoyl)benzyl alcohol

HRID 388759Notes

Reaction equation

HRID 388759 reaction equation
[Si](C([O:17][CH:18]([Si](C(C)(C)C)(C)C)[C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=1)C1C=C(Cl)C=C(Cl)C=1)(C(C)(C)C)(C)C.C([Li])CCC.[Cl:39][C:40]1[CH:48]=[CH:47][C:43]([C:44](Cl)=[O:45])=[CH:42][CH:41]=1.Cl>CCCCCC.O1CCCC1>[Cl:25][C:23]1[CH:24]=[C:19]([CH:20]=[C:21]([Cl:26])[C:22]=1[C:44](=[O:45])[C:43]1[CH:47]=[CH:48][C:40]([Cl:39])=[CH:41][CH:42]=1)[CH2:18][OH:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 85014-Chlorobenzoyl chlorideHCID 67042253t-Butyldimethylsilyl-3,5-dichlorobenzyl etherHCID 178418339Butyllithium

Product 1

HCID 28177663,5-Dichloro-4-(4-chlorobenzoyl)benzyl alcohol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

React t-Butyldimethylsilyl-3,5-dichlorobenzyl ether (858.A1) (1 mole) with n-Butyllithium 1.6M solution in hexane followed by 4-Chlorobenzoyl chloride, (1.01 mole), in Tetrahydrofuran, while cold and treat the intermediate with aqueous Hydrochloric acid to give 3,5-dichloro-4-(4-chlorobenzoyl)benzyl alcohol (858.B).

Sources & evidence

ORD record
ord-45edfd694f564fa8b228719c472b9a55
Source dataset
uspto-grants-2013_02
Patent number
US08377973B2

Reaction notes

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