Tert-Butylamine → 4-Decyloxycarbonyl-4'-hydroxybiphenyl

HRID 442593Notes

Reaction equation

HRID 442593 reaction equation
[CH2:1]([OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].CC([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28](O)=[O:29])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)=O.C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.C(N)(C)(C)C>O1CCCC1>[CH2:1]([O:11][C:28]([C:25]1[CH:24]=[CH:23][C:22]([C:19]2[CH:20]=[CH:21][C:16]([OH:15])=[CH:17][CH:18]=2)=[CH:27][CH:26]=1)=[O:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 5

HCID 6385Tert-ButylamineHCID 81741-DecanolHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 6118364'-Acetoxy-biphenyl-4-carboxylic acid

Product 1

HCID 148475754-Decyloxycarbonyl-4'-hydroxybiphenylYield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of n-decanol (1.6 g) and 4-methylcarbonyloxy-4'-carboxybiphenyl (2.6 g) in tetrahydrofuran (50 ml) were added dicyclohexylcarbodiimide (1.4 g) and dimethylaminopyridine (0.5 g), followed by stirring at room temperature for 24 hours. Thereto was added 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 make 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 2.3 g).

Workup

  1. temperaturethe mixture was refluxed at 70° C. for 2 hours
  2. distillationAfter the solvent was distilled off
  3. additiondilute hydrochloric acid was added
  4. extractionthe solution was extracted with diethyl ether
  5. distillationAfter the solvent was distilled off
  6. washthe residue was washed with hexane
  7. customrecrystallized from water/ethanol (1/9) solution

Sources & evidence

ORD record
ord-e60debf559bd49ddaf67dcd77e170b49
Source dataset
uspto-grants-1999_04
Patent number
US05891359

Reaction notes

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