Hydrochloric Acid → HCID 19074975, compound

HRID 964972Notes

Reaction equation

HRID 964972 reaction equation
[CH:1]([C:3]1[C:8]2[CH:9]=[CH:10][CH:11]([CH2:13][CH2:14][CH2:15][C:16]([O:18]C)=[O:17])[O:12][C:7]=2[C:6]([O:20][CH3:21])=[C:5]([O:22][CH3:23])[CH:4]=1)=[O:2].[OH-].[Na+].Cl.[Na+].[Cl-]>O1CCCC1>[CH:1]([C:3]1[C:8]2[CH:9]=[CH:10][CH:11]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[O:12][C:7]=2[C:6]([O:20][CH3:21])=[C:5]([O:22][CH3:23])[CH:4]=1)=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 54231074HCID 54231074, compound

Product 1

HCID 19074975HCID 19074975, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

1.5 g of methyl (RS)-4-(5-formyl-7,8-dimethoxy-2H-1-benzopyran-2-yl)-butyrate were dissolved in 10 ml of tetrahydrofuran under argon and then treated with 1 ml of 1N NaOH and stirred at 20° C. for 1.5 hrs. The reaction mixture was acidified with 9 ml of 1N HCl, saturated with NaCl and extracted with 2×20 ml of ethyl acetate. The crude product was chromatographed on silica gel in ethyl acetate and chromatographed from toluene/hexane 1:1 There was obtained (RS)-4-(5-formyl-7,8-dimethoxy-2H-1-benzopyran-2-yl)-butyric acid as white crystals.

Workup

  1. extractionextracted with 2×20 ml of ethyl acetate
  2. customThe crude product was chromatographed on silica gel in ethyl acetate
  3. customchromatographed from toluene/hexane 1:1 There

Sources & evidence

ORD record
ord-48f3188e72ec4a9b8f1834ec806b138b
Source dataset
uspto-grants-1998_06
Patent number
US05773446

Reaction notes

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