Lithium Hydroxide → 4-METHYLTETRAHYDRO-2H-PYRAN-4-CARBOXYLIC ACID

HRID 1677392Notes

Reaction equation

HRID 1677392 reaction equation
C[O:2][C:3]([C:5]1([CH3:11])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[OH-].[Li+]>O1CCCC1.O>[CH3:11][C:5]1([C:3]([OH:4])=[O:2])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 11019135Methyl 4-methyloxane-4-carboxylate

Product 1

HCID 115718204-METHYLTETRAHYDRO-2H-PYRAN-4-CARBOXYLIC ACIDYield 90.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-methyl-tetrahydro-pyran-4-carboxylic acid methyl ester (3.64 g, 23 mmol) in tetrahydrofuran (136 ml) was treated with a solution of lithium hydroxide (4.83 g, 115 mmol) in deionized water (27 ml). The reaction mixture was heated to 50° C. for overnight and then partitioned between EtOAc/water. The aqueous phase was collected and then partitioned between EtOAc/ice cold 1N HCl. The organic layers were dried over MgSO4, filtered, and concentrated providing 3 grams (90%) of 4-methyl-tetrahydro-pyran-4-carboxylic acid.

Workup

  1. custompartitioned between EtOAc/water
  2. customThe aqueous phase was collected
  3. custompartitioned between EtOAc/ice cold 1N HCl
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4fa9bdc14744440b91388a0467c9f43c
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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