Lithium Hydroxide → Oxane-4-carboxylic acid

HRID 12938

Reaction equation

HRID 12938 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9]C)=[O:8])[CH2:3][CH2:2]1.[Li+].[OH-]>C(O)C>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

Product 1

HCID 219302Oxane-4-carboxylic acidYield 94.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl tetrahydro-2H-pyran-4-carboxylate (270 g, 1.87 mol) was diluted in ethanol (2 L). A 1M aqueous LiOH solution (1870 ml, 1.87 mol) was added (slight exotherm) at RT and the reaction was stirred for 3 hrs. The reaction mixture was concentrated to ca. 1 L and acidified to pH 2 with 5M HCl solution. The aqueous solution was extracted with ethyl acetate (3×600 ml) and the organic layer was dried (MgSO4) and evaporated to dryness to give a white solid (230.3 g, 94%).

Workup

  1. concentrationThe reaction mixture was concentrated to ca. 1 L
  2. extractionThe aqueous solution was extracted with ethyl acetate (3×600 ml)
  3. dry with materialthe organic layer was dried (MgSO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-76e9fb2770784b0a8abd2575d9391bec
Source dataset
uspto-grants-2010_06
Patent number
US07728035B2

Linked notes

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