Phenol → Methyl-4-(trans-2-decenyloxy)-benzoate

HRID 413629Notes

Reaction equation

HRID 413629 reaction equation
C1(O)C=CC=CC=1.C(O)/C=C/CCCCCCC.CCOC(/N=N/C(OCC)=O)=O.[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]/[CH:42]=[CH:43]/[CH2:44][CH2:45][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 53649422-Decenol, (2E)-HCID 5462977Diethyl azodicarboxylate

Product 1

HCID 18521070Methyl-4-(trans-2-decenyloxy)-benzoateYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Phenol 34 (486 mg, 3.2 mmol), 2-decenol 26g (500 mg, 3.2 mmol), TPP (965 mg, 3.68 mmol), and DEAD (641 mg, 3.68 mmol) in 32 ml 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 95/5-90/10 (v/v, Hex/EtOAc). Evaporation of solvent yielded 603 mg (65%) of colorless needles.

Workup

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

Sources & evidence

ORD record
ord-3ccde8b6eb0e44c180f0d1201683a9ce
Source dataset
uspto-grants-2003_05
Patent number
US06569504B1

Reaction notes

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