Sodium Hydroxide → 3-(Undec-4z-enyloxy)benzoic acid

HRID 907396Notes

Reaction equation

HRID 907396 reaction equation
[OH-].[Na+].[CH2:3]([O:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([O:20]C)=[O:19])[CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>CO>[CH2:3]([O:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([OH:20])=[O:19])[CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 57939201HCID 57939201, compound

Product 1

HCID 579392143-(Undec-4z-enyloxy)benzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4 mL of 1 N sodium hydroxide solution (4.0 mmol) are added portionwise to 1.14 g of 15 (3.74 mmol) in methanol (30 mL). The solution is refluxed overnight. A further 4 mL of 1 N sodium hydroxide solution are added, and the mixture is refluxed for a further 1 hour 30 minutes. After evaporating off the solvent, the reaction medium is acidified with 0.5 N HCl and extracted with DCM. 1.04 g of a yellow oil are obtained, i.e. a yield of 96%.

Workup

  1. temperatureThe solution is refluxed overnight
  2. temperaturethe mixture is refluxed for a further 1 hour 30 minutes
  3. customAfter evaporating off the solvent
  4. extractionextracted with DCM

Sources & evidence

ORD record
ord-f95710e3af6b4e62b9c18928dfd8f6f6
Source dataset
uspto-grants-2011_09
Patent number
US08013132B2

Reaction notes

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