tert-Butyl hydroperoxide → 2,3-Difluoro-4-octyloxyphenyl 4-hexyloxybenzoate

HRID 6331

Reaction equation

HRID 6331 reaction equation
[CH2:1]([O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CN(C1C=CC=CN=1)C.[F:26][C:27]1[C:32]([F:33])=[C:31]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:30]=[CH:29][C:28]=1O.FC(C(F)CCCCC)COC1C=CC=CC=1.C(OOC(C)(C)C)(C)(C)C.[Li].C(OO)(C)(C)C.C([Li])CCC.C1(N=C=NC2CCCCC2)CCCCC1>CCOCC.ClCCl>[CH2:1]([O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[C:32]([F:33])[C:27]=2[F:26])=[O:13])=[CH:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

11

Reactant 8

HCID 6410tert-Butyl hydroperoxideHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 708344-(Hexyloxy)benzoic acidHCID 147667032,3-Difluoro-4octyloxyphenolHCID 191036322,3-DifluorooctyloxybenzeneHCID 86747250CID 86747250HCID 178418339Butyllithium

Product 1

HCID 191037182,3-Difluoro-4-octyloxyphenyl 4-hexyloxybenzoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.1 mol of 4-hexyloxybenzoic acid, 0.01 mol of dimethylaminopyridine and 0.1 mol of 2,3-difluoro-4octyloxyphenol (preparable from 2,3-difluorooctyloxybenzene by lithiation at -70° to -80° and dropwise addition of a solution of lithium t-butylperoxide in ether prepared from 0.12 mol of t-butyl hydroperoxide and 0.12 mol of butyllithium) are introduced into 150 ml of dichloromethane, a solution of 0.1 mol of dicyclohexylcarbodiimide in 30 ml of dichloromethane is added dropwise with stirring at 10o, and the mixture is subsequently stirred at room temperature for 15 hours. The mixture is filtered through silica gel, the solvent is evaporated, and 2,3-difluoro-4-octyloxyphenyl 4-hexyloxybenzoate is obtained as the residue.

Workup

  1. filtrationThe mixture is filtered through silica gel
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-82e83c02b9134508a72b2b79ba90c519
Source dataset
uspto-grants-1993_09
Patent number
US05248447

Linked notes

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