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Benzyl Alcohol → Di-tert-butyl ether

HRID 1377109
Notes
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Reaction equation

HRID 1377109 reaction equation
[CH2:1](O)[C:2]1[CH:7]=CC=C[CH:3]=1.[CH3:9][C:10](=[CH2:12])[CH3:11].C(NC(=[O:23])C(Cl)(Cl)Cl)(C)(C)C.B(F)(F)F.CCOCC>ClCCl.P(=O)(O)(O)O.B(F)(F)F.CCOCC.C1CCCCC1.C1CCCCC1.ClCCl.C(Cl)(Cl)Cl>[C:10]([O:23][C:2]([CH3:1])([CH3:3])[CH3:7])([CH3:11])([CH3:9])[CH3:12]
ParticipantsProcedureSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 244Benzyl AlcoholHCID 8000Boron trifluoride etherateHCID 8255IsobutyleneHCID 304045N-tert-butyl-2,2,2-trichloroacetamide

Product 1

HCID 22541Di-tert-butyl ether

Reagents, catalysts & solvents 5

HCID 6212ChloroformSolvent
HCID 6344
Dichloromethane
Solvent
HCID 8078CyclohexaneSolvent
HCID 21916607Dichloromethane cyclohexaneSolvent
HCID 86751212Phosphoric acid boron trifluoride etherateSolvent

Procedure

Benzyl alcohol derivatives E6 dissolved in dichloromethane or chloroform are treated with isobutylene in phosphoric acid-boron trifluoride etherate for about 1 to 3 hours at about -78° C. to -60° C. then 18 hours at room temperature or with tert-butyl-2,2,2-trichloroacetamidate in the presence of a catalytic amount of boron trifluoride etherate in cyclohexane or in a mixture of cyclohexane-dichloromethane at room temperature for about 18-24 hours to produce tert-butyl ether derivatives E7.

Sources & evidence

ORD record
ord-c509cebbb1cd4e558a7b255e9e074523
Source dataset
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05663448

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes