Sodium Hydroxide → HCID 66618720, compound

HRID 406327Notes

Reaction equation

HRID 406327 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([C:10]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[C:13]([O:19][CH3:20])=[CH:12][C:11]=1[CH3:21])[C:6]([O:8]C)=[O:7].[OH-].[Na+]>CO.O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([C:10]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[C:13]([O:19][CH3:20])=[CH:12][C:11]=1[CH3:21])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66618902HCID 66618902, compound

Product 1

HCID 66618720HCID 66618720, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-chloro-2-(5-isopropyl-4-methoxy-2-methylphenyl)pentanoate (7.7 g) was dissolved in a mixed solvent of methanol (25 mL) and tetrahydrofuran (25 mL). A 5 N sodium hydroxide solution (22 mL) was added and the mixture was stirred at room temperature for four hours. The reaction solution was concentrated under reduced pressure and water was added, followed by washing with heptane. The aqueous layer was made acidic with 5 N hydrochloric acid, followed by extraction with tert-butyl methyl ether. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and the organic layer was concentrated under reduced pressure to obtain 5-chloro-2-(5-isopropyl-4-methoxy-2-methylphenyl)pentanoic acid (6.2 g).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure and water
  2. additionwas added
  3. washby washing with heptane
  4. extractionfollowed by extraction with tert-butyl methyl ether
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe drying agent was separated by filtration
  8. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-42e1e5f5eabb4e5ab76ccdce9ef70895
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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