Hydrochloric Acid → HCID 54696989, compound

HRID 434087Notes

Reaction equation

HRID 434087 reaction equation
[CH2:1]([O:7][C:8]1[C:9](=[O:26])[O:10][C:11]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]([O:23]CC)=[O:22])[C:12]=2[C:13]=1[OH:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[Na+].Cl>C(O)C>[CH2:1]([O:7][C:8]1[C:9](=[O:26])[O:10][C:11]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]([OH:23])=[O:22])[C:12]=2[C:13]=1[OH:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54696882HCID 54696882, compound

Product 1

HCID 54696989HCID 54696989, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

25 ml of ethanol was added to 3.64 g (0.01 mol) of 3-hexyloxy-4-hydroxy-5-ethoxycarbonylmethoxy-2H-1-benzopyran-2-one, and 25 ml of an aqueous 1 mol/L sodium hydroxide solution was added under ice cooling, followed by continuous stirring at room temperature for 4 hours. The reaction solution was added to 26 ml of hydrochloric acid having a concentration of 1 mol/L, and after extracting twice with 50 ml of ethyl acetate, the extract was dried over magnesium sulfate. After filtering the ethyl acetate solution, the filtrate was concentrated under reduced pressure, and the resulting crude product was recrystallized from methanol to obtain 2.4 g of the titled compound (yield: 74%)

Workup

  1. additionwas added under ice cooling
  2. extractionafter extracting twice with 50 ml of ethyl acetate
  3. dry with materialthe extract was dried over magnesium sulfate
  4. filtrationAfter filtering the ethyl acetate solution
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe resulting crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-9e710f96dd394c929bf9b206bdbf9fee
Source dataset
uspto-grants-2003_12
Patent number
US06670391B2

Reaction notes

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