Phenol → Methyl-4-(trans-5-decenyloxy)-benzoate

HRID 413632Notes

Reaction equation

HRID 413632 reaction equation
CCOC(/N=N/C(OCC)=O)=O.C1(O)C=CC=CC=1.C(O)CCC/C=C/CCCC.[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][CH2:44]/[CH:45]=[CH:46]/[CH2:47][CH2:48][CH2:49][CH3:50])=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 4189536Methyl 4-(octadecyloxy)benzoateHCID 52832925-Decen-1-ol, (5E)-HCID 5462977Diethyl azodicarboxylate

Product 1

HCID 18521058Methyl-4-(trans-5-decenyloxy)-benzoateYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

DEAD (256 mg, 1.47 mmol), phenol 34 (194 mg, 1.28 mmol), alcohol 26j (200 mg, 1.28 mmol), and TPP (386 mg, 1.47 mmol) in 13 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 266 mg (72%) 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-f88af62debeb4184a7fbf0620da384ed
Source dataset
uspto-grants-2003_05
Patent number
US06569504B1

Reaction notes

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