Water → 2-(1,3-Dimethoxypropan-2-yloxy)acetic acid

HRID 2425447Notes

Reaction equation

HRID 2425447 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([OH:8])[CH2:5][O:6][CH3:7].I[CH2:10][C:11]([O-:13])=[O:12].[Na+].[H-].[Na+].O>O1CCCC1>[CH3:1][O:2][CH2:3][CH:4]([O:8][CH2:10][C:11]([OH:13])=[O:12])[CH2:5][O:6][CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 5239Sodium IodoacetateHCID 121901,3-Dimethoxy-2-propanolHCID 24758Sodium hydride

Product 1

HCID 866278142-(1,3-Dimethoxypropan-2-yloxy)acetic acidYield 38.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1,3-dimethoxy-2-propanol (361.5 mg, Tyger) in tetrahydrofuran (4 ml) was added with sodium iodoacetate (624.6 mg, Spectrum), and successively added with sodium hydride (198 mg, Wako Pure Chemical Industries) as several portions at 0° C., and the mixture was stirred at the same temperature for 30 minutes, and then further stirred at room temperature for 15.5 hours. The reaction mixture was cooled again to 0° C., and then carefully added with water and then with chloroform, and the organic layer was separated. The aqueous layer was acidified (pH 4) with 1 N hydrochloric acid, and extracted three times with chloroform, and the combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure to obtain the title compound (206.5 mg).

Workup

  1. stirringfurther stirred at room temperature for 15.5 hours
  2. customwith chloroform, and the organic layer was separated
  3. extractionextracted three times with chloroform
  4. washthe combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThen, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-051e20871f6a47fb877f6985daa99780
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Reaction notes

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