Hydrochloric Acid → 6-Hydroxy-3-coumaranone

HRID 1194810Notes

Reaction equation

HRID 1194810 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[C:6]1([CH:13]=[CH:12][CH:11]=[C:9]([OH:10])[CH:8]=1)[OH:7].[Cl-].[Al+3].[Cl-].[Cl-].Cl>[N+](C1C=CC=CC=1)([O-])=O>[OH:7][C:6]1[CH:8]=[C:9]2[C:11]([C:3](=[O:4])[CH2:2][O:10]2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5054ResorcinolHCID 6577Chloroacetyl chloride2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 2357176-Hydroxy-3-coumaranone

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

Chloroacetyl chloride (28.25 g) was added dropwise over 1.5 hours to a stirred mixture of resorcinol (Aldrich Chemical Company) (22 g), aluminum chloride (33.3 g) and nitrobenzene (250 cc), the temperature being kept at 50°-55° C. during the chloroacetyl chloride addition and for an additional 15 minutes thereafter. The solution was then cooled and poured into an excess of ice and dilute hydrochloric acid. The organic layer was retained and extracted with aqueous sodium hydroxide (300 ml, 1M). The alkaline extract was acidified with concentrated hydrochloric acid and filtered to give 6-hydroxycoumaran-3-one, m.p. --238°-240° C.

Workup

  1. temperatureThe solution was then cooled
  2. extractionextracted with aqueous sodium hydroxide (300 ml, 1M)
  3. extractionThe alkaline extract
  4. filtrationfiltered

Sources & evidence

ORD record
ord-f45512f6bf1d475cbf9a917846cf657d
Source dataset
uspto-grants-1989_03
Patent number
US04816473

Reaction notes

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