Sodium Hydroxide → 3-(1-tert-Butoxycarbonyl-1-methylethoxy)phenylacetic Acid

HRID 480708Notes

Reaction equation

HRID 480708 reaction equation
C([O:4][C:5]([CH2:7][C:8]1[CH:9]=[C:10]([CH:22]=[CH:23][CH:24]=1)[O:11][C:12]([CH3:21])([CH3:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:6])C=C.[OH-].[Na+]>CO.O1CCCC1>[C:16]([O:15][C:13]([C:12]([CH3:21])([O:11][C:10]1[CH:9]=[C:8]([CH2:7][C:5]([OH:6])=[O:4])[CH:24]=[CH:23][CH:22]=1)[CH3:20])=[O:14])([CH3:17])([CH3:18])[CH3:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18766493tert-Butyl 2-[3-(Allyloxycarbonylmethyl)phenoxy]-2-methylpropionate

Product 1

HCID 187664143-(1-tert-Butoxycarbonyl-1-methylethoxy)phenylacetic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 2-[3-(allyloxycarbonylmethyl)phenoxy]-2-methylpropionate (3.35 g, 10.62 mmol) was dissolved in methanol (40 mL) and tetrahydrofuran (40 mL). Subsequently, an aqueous 2M sodium hydroxide solution (40 mL) was added thereto, and the mixture was stirred for three hours at room temperature. The resultant mixture was concentrated under reduced pressure, and the resultant concentrate was acidified with 3M hydrochloric acid. The mixture was extracted with chloroform, followed by drying over sodium sulfate and concentration under reduced pressure, whereby the target compound was obtained (2.98 g, 10.12 mmol, 95.5%).

Workup

  1. concentrationThe resultant mixture was concentrated under reduced pressure
  2. concentrationthe resultant concentrate
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialby drying over sodium sulfate and concentration under reduced pressure, whereby the target compound
  5. customwas obtained (2.98 g, 10.12 mmol, 95.5%)

Sources & evidence

ORD record
ord-63ebdbbe60e9437a88813724a30867c2
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

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