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

HRID 369533
Notes
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Reaction equation

HRID 369533 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 3283
Diethyl Ether
Solvent

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-6fce36808b4841f78ea78c017314a9bc
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06139771

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes