Water → 7-beta-Galactosylcoumarin-3-carboxylic acid

HRID 543866Notes

Reaction equation

HRID 543866 reaction equation
[OH-].[K+].O.[C@@H:4]1([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[C:20]([C:26]([O:28]CC)=[O:27])[C:21](=[O:25])[O:22]3)=[CH:17][CH:16]=2)[O:12][C@H:11]([CH2:13][OH:14])[C@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6]>CO>[C@@H:4]1([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[C:20]([C:26]([OH:28])=[O:27])[C:21](=[O:25])[O:22]3)=[CH:17][CH:16]=2)[O:12][C@H:11]([CH2:13][OH:14])[C@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 22809745Ethyl 7-beta-galactosylcoumarin-3-carboxylate

Product 1

HCID 228097447-beta-Galactosylcoumarin-3-carboxylic acidYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 24 g of potassium hydroxide, 80 ml of water, 240 ml of methanol, and 20 g (0.035 mol) of ethyl 7-β-galactosylcoumarin-3-carboxylate [Supra, Burd et al, Clin. Chem.] was prepared. The methanol was removed under reduced pressure. The concentrated aqueous solution was acidified to pH 2.6 with concentrated hydrochloric acid. The white precipitate was collected, washed with cold water, and recrystallized from hot water. The crystals were collected, washed with acetone, and dried at 80° C. for 1 hour. This gave 12 g (54% yield) of 7-β-galactosylcoumarin-3-carboxylic acid as white crystals, mp 250°-255° C.

Workup

  1. customwas prepared
  2. customThe methanol was removed under reduced pressure
  3. customThe white precipitate was collected
  4. washwashed with cold water
  5. customrecrystallized from hot water
  6. customThe crystals were collected
  7. washwashed with acetone
  8. customdried at 80° C. for 1 hour

Sources & evidence

ORD record
ord-43b907e8715c46ecb4fb725e824a01a0
Source dataset
uspto-grants-1984_05
Patent number
US04447529

Reaction notes

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