Triethylamine → 4-n-Undecanoyloxy-4'-hydroxy-biphenyl

HRID 442592Notes

Reaction equation

[CH3:1][C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=[O:3].C(N(CC)CC)C.[C:25](Cl)(=O)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]CC.CN(C1C=CC=CN=1)C>C(Cl)Cl>[C:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)(=[O:3])[CH2:1][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-methylcarbonyloxy-4'-hydroxybiphenyl (2.3 g) and triethylamine (1.1 g) in methylene chloride (50 ml) was gradually added dropwise undecanoyl chloride (n-C10H21COCl) (2.1 g). Dimethylaminopyridine (0.3 g) was further added thereto and the mixture was stirred for 24 hours. After the solvent was distilled off, the residue was added to tetrahydrofuran containing tert-butylamine and the mixture was refluxed at 70° C. for 2 hours and hydrolyzed. After the solvent was distilled off, dilute hydrochloric acid was added to the residue to render the solution neutral and the solution was extracted with diethyl ether. After the solvent was distilled off, the residue was washed with hexane and recrystallized from water/ethanol (1/9) solution to obtain the titled compound (about 1.4 g).

Workup

distillationAfter the solvent was distilled off
additionthe residue was added to tetrahydrofuran
additioncontaining tert-butylamine
distillationAfter the solvent was distilled off
additiondilute hydrochloric acid was added to the residue
extractionthe solution was extracted with diethyl ether
distillationAfter the solvent was distilled off
washthe residue was washed with hexane
customrecrystallized from water/ethanol (1/9) solution

Sources & evidence

ORD record: ord-67403f27f5e745d7a42c1dd6a376f3cb
Source dataset: uspto-grants-1999_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05891359

Reaction notes

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