Hydrochloric Acid → 5-(ethoxycarbonyl)-3-hydroxy-9-oxo-9H-xanthene-2-propanoic acid

HRID 982449Notes

Reaction equation

HRID 982449 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:9][C:8]=1[O:25]CCCCCCCCCC)C.[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)(=O)[C:42](Cl)=[O:43].Cl>C(Cl)Cl>[CH2:23]([O:22][C:20]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[O:13][C:10]1[CH:9]=[C:8]([OH:25])[C:7]([CH2:6][CH2:5][C:4]([OH:3])=[O:36])=[CH:12][C:11]=1[C:42]2=[O:43])=[O:21])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 157180622-(Decyloxy)-4-[2-(ethoxycarbonyl)phenoxy]benzenepropanoic acid ethyl ester

Product 1

HCID 200677635-(ethoxycarbonyl)-3-hydroxy-9-oxo-9H-xanthene-2-propanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.7 g of 2-(decyloxy)-4-[2-(ethoxycarbonyl)phenoxy]benzenepropanoic acid ethyl ester in methylene chloride at room temperature were added 0.187 g of aluminum chloride followed by 0.122 ml of oxalyl chloride. After stirring for approximately 1 hour, the mixture was poured into a combination of ice and hydrochloric acid. After stirring for approximately 1 hour, the layers were separated and the organic layer was dried and concentrated in vacuo. The material was used without further purification in the subsequent reaction.

Workup

  1. stirringAfter stirring for approximately 1 hour
  2. customthe layers were separated
  3. customthe organic layer was dried
  4. concentrationconcentrated in vacuo
  5. customThe material was used without further purification in the subsequent reaction

Sources & evidence

ORD record
ord-d61cf8980657401c93329b9fb9a85abe
Source dataset
uspto-grants-1991_02
Patent number
US04996230

Reaction notes

Loading…