Sodium Bicarbonate → 2-(4-hydroxybutyloxy)acetic Acid Tert-Butyl Ester

HRID 1271249Notes

Reaction equation

HRID 1271249 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13]C1CCCCO1)([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CO>[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 693544612-[4-(2-tetrahydropyranyloxy)butyloxy]acetic Acid Tert-Butyl Ester

Product 1

HCID 865924582-(4-hydroxybutyloxy)acetic Acid Tert-Butyl EsterYield 66.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 36.21 g of 2-[4-(2-tetrahydropyranyloxy)butyloxy]acetic acid tert-butyl ester in 360 ml of methanol, 47.77 g of p-toluenesulfonic acid monohydrate was added. After stirring at room temperature for 30 minutes, the reaction solution was neutralized with an aqueous sodium hydrogen carbonate solution and the solvent was evaporated under reduced pressure. The residue was diluted with water, extracted with diethyl ether, washed with water and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 17.02 g of the desired compound as a colorless oily substance.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with diethyl ether
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-388b95db04074cf08e2086b9ced83f2a
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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