Sodium Hydroxide → HCID 9949633, compound

HRID 1018115Notes

Reaction equation

HRID 1018115 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[O:18][CH2:17][CH2:16][C:15]3([CH2:23][O:24][CH3:25])[CH3:22])=[CH:6][CH:5]=1.[OH-].[Na+]>C1COCC1.C(O)C>[CH3:25][O:24][CH2:23][C:15]1([CH3:22])[C:14]2[C:19](=[CH:20][CH:21]=[C:12]([C:11]#[C:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:26])=[O:2])=[CH:9][CH:8]=3)[CH:13]=2)[O:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70002702HCID 70002702, compound

Product 1

HCID 9949633HCID 9949633, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

625 mg (1.78 mmol) of 4-(4-methoxymethyl-4-methyl-chroman-6-ylethynyl)-benzoic acid methyl ester was dissolved in 9 ml of THF/ethanol (1/1) and treated with 2.34 ml of 3N NaOH (4 eq.). The reaction flask was kept in the dark and stirring continued for 18 h at room temperature. The mixture was then poured onto crushed ice/ HCl, extracted twice with diethylether, the organic phase was washed with water, dried over magnesium sulfate, filtrated and the solvent was evaporated. Crystallization from ethylacetate yielded 545 mg of the title product as white crystals of m.p. 202-203° C.

Workup

  1. additionThe mixture was then poured
  2. extractionextracted twice with diethylether
  3. washthe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltrated
  6. customthe solvent was evaporated
  7. customCrystallization from ethylacetate

Sources & evidence

ORD record
ord-1410b483e4494fee9495200e88875c9b
Source dataset
uspto-grants-2002_11
Patent number
US06479670B1

Reaction notes

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