Sodium Hydroxide → Oxane-4-carboxylic acid

HRID 2088910Notes

Reaction equation

HRID 2088910 reaction equation
[OH-].[Na+].[O:3]1[CH2:8][CH2:7][CH:6]([C:9]([O:11]C)=[O:10])[CH2:5][CH2:4]1>CO.O>[O:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

Product 1

HCID 219302Oxane-4-carboxylic acidYield 69.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

Add 40% w/w sodium hydroxide in water (264.5 mL, 1.15 eq) to a solution of methyl tetrahydro-2H-pyran-4-carboxylate (500 g, 3.47 mol) in methanol (2.26 L). Stir at 50° C. for seven hours. Evaporate solvent, dissolve residue in water (2 L) and wash with methyl-tert-butyl ether (2×1.2 L). Add aqueous 35% hydrochloric acid to the aqueous layer (adjusting pH to 4) and extract with methyl tert-butyl ether (2×1.2 L). Dry over anhydrous magnesium sulfate and concentrate in vacuo. As material still contains water, dissolve the solid in dichloromethane and discard the aqueous layer. Dry the organics with anhydrous sodium sulfate and concentrate in vacuo to give tetrahydro-2H-pyran-4-carboxylic acid (312.76 g, 69%). 1H NMR (300 MHz, DMSO-d6) δ 11.21 (br s, 1H), 3.97 (m, 2H), 3.44 (m, 2H), 2.56 (m, 1H), 1.81 (m, 4H).

Workup

  1. washwash with methyl-tert-butyl ether (2×1.2 L)
  2. extractionAdd aqueous 35% hydrochloric acid to the aqueous layer (adjusting pH to 4) and extract with methyl tert-butyl ether (2×1.2 L)
  3. dry with materialDry over anhydrous magnesium sulfate
  4. concentrationconcentrate in vacuo
  5. dissolutionAs material still contains water, dissolve the solid in dichloromethane
  6. dry with materialDry the organics with anhydrous sodium sulfate
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b63d53bbd37543a3b5ca0055aecb7527
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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