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

HRID 369532

Reaction equation

HRID 369532 reaction equation
C1(O)C=CC=CC=1.C(O)C=CCCCCCCC.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 876302-Decen-1-olHCID 4189536Methyl 4-(octadecyloxy)benzoateHCID 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 26 g (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-18a140bcba8640bf90b50ad97f4e25ab
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Linked notes

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