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

HRID 369534

Reaction equation

HRID 369534 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-9a90c8df748145509ba2b474a6a4236b
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Linked notes

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