Lithium Hydroxide → 2-[6-(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)hexyloxy]benzenepropanoic acid

HRID 327990Notes

Reaction equation

HRID 327990 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:29]=[CH:28][C:22]2[C:23](=[O:27])[CH2:24][CH2:25][O:26][C:21]=2[C:20]=1[CH2:30][CH2:31][CH3:32].[OH-].[Li+]>O1CCCC1>[O:27]=[C:23]1[C:22]2[CH:28]=[CH:29][C:19]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[CH2:5][CH2:4][C:3]([OH:33])=[O:2])=[C:20]([CH2:30][CH2:31][CH3:32])[C:21]=2[O:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 540316242-[6-(3,4-Dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)hexyloxy]benzenepropanoic acid methyl ester

Product 1

HCID 199219642-[6-(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)hexyloxy]benzenepropanoic acidYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.65 g (1.44 mmol) of 2-[6-(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)hexyloxy]benzenepropanoic acid methyl ester, 2 mL of 3N aqueous lithium hydroxide, and 30 mL of tetrahydrofuran was stirred at room temperature for 24 hr and then concentrated in vacuo. The residue was diluted with water and extracted 3 times with ether (the ether extracts were discarded). The aqueous alkaline solution was acidified with 3N HCl and worked-up with ether in the usual manner. The oily residue was chromatographed on silica gel. Elution with 2:1 toluene-ethyl acetate containing acetic acid afforded 0.5 g (79.3%) of 2-[6-(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)hexyloxy]benzenepropanoic acid as viscous, colorless oil.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted 3 times with ether (the ether extracts
  4. customThe oily residue was chromatographed on silica gel
  5. washElution with 2:1 toluene-ethyl acetate
  6. additioncontaining acetic acid

Sources & evidence

ORD record
ord-8acd5fe97cd04dc8904acd4de2e201e3
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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