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

HRID 369535

Reaction equation

HRID 369535 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-e52e70a0fad94010ab6d00296b042670
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Linked notes

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