Citric Acid → 7-Hydroxycoumarin-4-acetic acid

HRID 973743Notes

Reaction equation

HRID 973743 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5](O)=O)O.S(=O)(=O)(O)O.[C:19]1(O)C=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=1>>[OH:25][C:21]1[CH:22]=[C:23]2[C:5]([C:3]([CH2:2][C:1]([OH:13])=[O:12])=[CH:8][C:9](=[O:10])[O:11]2)=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 311Citric AcidHCID 1118Sulfuric Acid2×HCID 5054Resorcinol

Product 1

HCID 53384907-Hydroxycoumarin-4-acetic acid

Conditions

Temperature
70 °C

Procedure

84 g of citric acid and 112 ml of concentrated sulfuric acid were stirred for one hour at ambient temperature and then heated progressively to 70° C. and maintained there for 35 minutes. The mixture was cooled to 0° C. and 34.56 g of 1,3-benzene diol and 44.8 ml of concentrated sulfuric acid were added. The mixture was maintained for 16 hours at 0° C. and then poured over ice. The crystallized product was separated off and dried under reduced pressure to obtain after crystallization from water, 22.77 g of the expected product melting at 210° C.

Workup

  1. temperaturemaintained there for 35 minutes
  2. temperatureThe mixture was cooled to 0° C.
  3. temperatureThe mixture was maintained for 16 hours at 0° C.
  4. additionpoured over ice
  5. customThe crystallized product was separated off
  6. customdried under reduced pressure
  7. customto obtain
  8. customafter crystallization from water, 22.77 g of the expected product melting at 210° C.

Sources & evidence

ORD record
ord-5d9f9fef7465434fa98489d2d6f19d6f
Source dataset
uspto-grants-1991_11
Patent number
US05064861

Reaction notes

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