Potassium Hydroxide → HCID 59815680, compound

HRID 1507739Notes

Reaction equation

HRID 1507739 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:13])([CH3:12])[C:8]([O:10]C)=[O:9].[OH-].[K+]>O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:13])([CH3:12])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59253200HCID 59253200, compound

Product 1

HCID 59815680HCID 59815680, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of methyl 3-(2-methoxyethoxy)-2,2-dimethylpropanoate (39) (1.83 g, 9.62 mmol) and KOH (2.16 g, 38.5 mmol) in water (20 mL) was stirred at RT for 3 days. The aqueous layer was washed with DCM (3×20 mL) and acidified to pH 1-2 with 6 M HCl (aq.) and extracted with DCM (3×20 mL). The combined organics were dried (MgSO4), filtered and concentrated in vacuo to afford 3-(2-methoxyethoxy)-2,2-dimethylpropanoic acid (40) (1.62 g, 96%) as colourless oil: 1H NMR (400 MHz, CDCl3) δ: 3.67-3.65 (m, 2H), 3.56-3.54 (m, 2H), 3.51 (s, 2H), 3.38 (s, 3H), 1.23 (s, 6H).

Workup

  1. washThe aqueous layer was washed with DCM (3×20 mL)
  2. extractionextracted with DCM (3×20 mL)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-177288a49c6640b296b9aadf9e668085
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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