Sodium Hydroxide → HCID 20373753, compound

HRID 1834659Notes

Reaction equation

HRID 1834659 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH:14]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[CH2:13][CH2:12][CH:11]1[CH:22]=[O:23].[OH-].[Na+]>CO>[CH:22]([CH:11]1[CH2:12][CH2:13][CH:14]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[CH:10]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:24])=[O:2])=[O:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21559474HCID 21559474, compound

Product 1

HCID 20373753HCID 20373753, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-formyl-5-(tetrahydropyran-2-yloxy)-cyclopentaneheptanoic acid methyl ester (23.64 g), described by J. Bagli and T. Bogri, Tetrahedron Letters, 3815 (1972), see also U.S. Pat. No. 3,773,795 issued November 20, 1973, in methanol (20 ml) is added 10% NaOH (33.5 ml). The reaction mixture is stirred under a nitrogen atmosphere at 40° C (bath temperature) for 18 hr. The mixture is cooled and the methanol is evaporated from the mixture. The residue is taken up in ether and the resulting mixture is washed with a small amount of water. The aqueous layer is acidified with acetic acid and extracted with ether. The ether extract is washed with water, dried and concentrated to yield the title compound, νmaxfilm 2700, 1712, 1125 and 1025 cm-1.

Workup

  1. temperatureThe mixture is cooled
  2. customthe methanol is evaporated from the mixture
  3. washthe resulting mixture is washed with a small amount of water
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washis washed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4ee5944b21db45b888046d2fdd20afdc
Source dataset
uspto-grants-1978_01
Patent number
US04070482

Reaction notes

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