Hydrochloric Acid → Oxane-4-carboxylic acid

HRID 1711185Notes

Reaction equation

HRID 1711185 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9]C)=[O:8])[CH2:3][CH2:2]1.Cl>[OH-].[Na+].CO.O>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

Product 1

HCID 219302Oxane-4-carboxylic acidYield 87%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

Methyl tetrahydro-2-H-pyran-4-carboxylate (400 μL, 3.00 mmol) was dissolved in a 5:1 mixture of 10M NaOH and MeOH (4.0 ml: 0.8 ml). The mixture was heated to 60° C. for 3 hours. After the reaction was complete, all volatiles were removed under high vacuum to leave a residual solid. The residue was dissolved in H2O and subsequently acidified to pH˜1 using aqueous HCl. The acidic aqueous phase was extracted with DCM and dried over Na2SO4. The solvent was removed to give tetrahydro-pyran-4-carboxylic acid (339 mg, 87%), which was used in the next step without further purification.

Workup

  1. customall volatiles were removed under high vacuum
  2. customto leave a residual solid
  3. extractionThe acidic aqueous phase was extracted with DCM
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-47b8db9ecf9e42f2ab310ae35b1a0f20
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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