Phenol → Methyl-4-(trans-4-decenyloxy)-benzoate

HRID 413631Notes

Reaction equation

HRID 413631 reaction equation
CCOC(/N=N/C(OCC)=O)=O.C1(O)C=CC=CC=1.C(O)CC/C=C/CCCCC.[CH3:31][O:32][C:33](=[O:59])[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]CCCCCCCC)=[CH:36][CH:35]=1>CCOCC>[CH3:31][O:32][C:33](=[O:59])[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43]/[CH:44]=[CH:45]/[CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 4189536Methyl 4-(octadecyloxy)benzoateHCID 5462977Diethyl azodicarboxylateHCID 5702619Dec-4-en-1-ol

Product 1

HCID 18521044Methyl-4-(trans-4-decenyloxy)-benzoateYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

DEAD (641 mg, 3.68 mmol), phenol 34 (487 mg, 3.2 mmol), alcohol 26i (500 mg, 3.2 mmol), and TPP (966 mg, 3.68 mmol) in 16 ml anhydrous ether were reacted according to the procedure for compound 35a. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc). Evaporation of the solvent yielded 748 mg (80%) of colorless liquid.

Workup

  1. customThe crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc)
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-aabf4a53aa2e4328af39e7245153793d
Source dataset
uspto-grants-2003_05
Patent number
US06569504B1

Reaction notes

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