Benzyl Alcohol → Di-tert-butyl ether

HRID 1377109Notes

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]

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 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolventHCID 21916607Dichloromethane cyclohexaneSolventHCID 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
Patent number
US05663448

Reaction notes

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