Acetic Acid → 2,3-Dihydro-alpha-methyl-1,4-benzodioxin-6-acetic acid

HRID 1626858Notes

Reaction equation

HRID 1626858 reaction equation
C1COCC1.O.[O:7]1[CH2:12][CH2:11][O:10][C:9]2[CH:13]=[CH:14][C:15]([CH:17]([CH3:23])[C:18]([O:20]CC)=[O:19])=[CH:16][C:8]1=2.[OH-].[Na+].C(O)(=O)C>O>[O:7]1[CH2:12][CH2:11][O:10][C:9]2[CH:13]=[CH:14][C:15]([CH:17]([CH3:23])[C:18]([OH:20])=[O:19])=[CH:16][C:8]1=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 18693671Ethyl 2-(2,3-dihydrobenzo[b][1,4]dioxin-7-yl)propanoateHCID 21881883Oxolane--water (1/1)

Product 1

HCID 100359452,3-Dihydro-alpha-methyl-1,4-benzodioxin-6-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the flask was added THF/H2O (1:1, 4 mL) followed by Ethyl 2-(2,3-dihydrobenzo[b][1,4]dioxin-7-yl)propanoate (133 mg, 0.563 mmol) and NaOH (30 mg, 0.750 mmol) at room temperature. The reaction mixture was stirred for 16 hrs at room temperature. The mixture was diluted with H2O (20 mL) and acidified with acetic acid (4 mL, pH=4) then extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. Colorless oil, yield: quantitative.

Workup

  1. extractionthen extracted with CH2Cl2
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c9d790bb0e34fe994ecffdba612a992
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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