Phenol → Methyl-4-(trans-3-decenyloxy)-benzoate

HRID 413630Notes

Reaction equation

HRID 413630 reaction equation
C1(O)C=CC=CC=1.C(O)C/C=C/CCCCCC.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][CH2:42]/[CH:43]=[CH: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 53524933-Decen-1-ol, (3E)-HCID 5462977Diethyl azodicarboxylate

Product 1

HCID 18521096Methyl-4-(trans-3-decenyloxy)-benzoateYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ester 34 (500 mg, 3.29 mmol), 3-decenol 26h (514 mg, 3.29 mmol), TPP (992 mg, 3.78 mmol), DEAD (658 mg, 3.78 mmol), and 33 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 810 mg (85%) of colorless liquid which was not quite pure. The product was used without further purification.

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-afc7ac3400cd44d7aa1b4f08fd254ee8
Source dataset
uspto-grants-2003_05
Patent number
US06569504B1

Reaction notes

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