Ethanol → Ethyl 10-chloroanthracene-1-carboxylate

HRID 2413660Notes

Reaction equation

HRID 2413660 reaction equation
[Cl:1][C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:16]([OH:18])=[O:17].OS(O)(=O)=O.[CH3:24][CH2:25]O>>[Cl:1][C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:16]([O:18][CH2:24][CH3:25])=[O:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 13375410HCID 13375410, compound

Product 1

HCID 21276219Ethyl 10-chloroanthracene-1-carboxylateYield 77%

Procedure

10-Chloroanthracene-1-carboxylic acid (37A, 17.3 g, 0.0674 mol), conc. H2SO4 (1.0 mL), and abs. EtOH (500 mL) was refluxed for 3 days using 4Å molecular sieves in a Soxhlet extractor to remove H2O. The solvent was removed and then partitioned between EtOAc and satd. NaHCO3. The solvent was then removed from the organic layer to give 14.86 g (77%) of ethyl 10-chloroanthracene-1-carboxylate, which was used without further purification.

Workup

  1. customto remove H2O
  2. customThe solvent was removed
  3. custompartitioned between EtOAc
  4. customThe solvent was then removed from the organic layer

Sources & evidence

ORD record
ord-3ca5081178aa4c0499fda9c720badb1f
Source dataset
uspto-grants-1988_01
Patent number
US04719049

Reaction notes

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