1-Octanol → Octyl4'-methoxycarbonyloxy-4-biphenylcarboxylate

HRID 651303

Reaction equation

HRID 651303 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([OH:39])=[O:38])=[CH:33][CH:32]=2)=[CH:27][CH:26]=1)=[O:23].[CH2:40](O)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:20][O:21][C:22]([O:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[O:38])=[CH:33][CH:32]=2)=[CH:29][CH:30]=1)=[O:23]

Participants

6

Reactant 4

HCID 9571-OctanolHCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 183284084'-Methoxycarbonyloxy-4-biphenylcarboxylic acid2×

Product 1

HCID 18328376Octyl4'-methoxycarbonyloxy-4-biphenylcarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of triphenylphosphine (3.78 g, 0.014 mol) in dry tetrahydrofuran (50 ml) was added to a stirred solution of compound 4 (3.92 g, 0.014 mol), octan-1-ol (1.88 g 0.014 mol) and diethyl azodicarboxylate (DEAD) (2.51 g 0.014 mol) in dry tetrahydrofuran (100 ml) under an atmosphere of dry nitrogen. The addition was such that the triphenylphosphine was added over 30 seconds in which time the solution became hot and the white solid (4) and orange colour (DEAD) disappeared. The resultant solution was stirred overnight, the solvent was removed in vacuo and the viscous, oily residue was purified by column chromatography (10% petrol/dichloromethane) to give a colourless solid which was recrystallised from ethanol to leave colourless plates.

Workup

  1. additionThe addition
  2. additionwas added over 30 seconds in which time the solution
  3. customthe solvent was removed in vacuo
  4. customthe viscous, oily residue was purified by column chromatography (10% petrol/dichloromethane)
  5. customto give a colourless solid which
  6. customwas recrystallised from ethanol
  7. customto leave colourless plates

Sources & evidence

ORD record
ord-21b90c025f3a4e54907e42cc3e272c2f
Source dataset
uspto-grants-2001_08
Patent number
US06278028B1

Linked notes

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