Acetic Anhydride → HCID 13066720, compound

HRID 1163997Notes

Reaction equation

HRID 1163997 reaction equation
C(OC(=O)C)(=O)C.O[C:9]1[C:14]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:23][CH2:24][C:25]([OH:27])=[O:26]>C1C=CC=CC=1>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:9]=1[O:27][C:25](=[O:26])[CH2:24][CH2:23]2

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13066679HCID 13066679, compound

Product 1

HCID 13066720HCID 13066720, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Acetic anhydride (10 ml) was added to a solution of 3-[2-hydroxy-3-(2-chlorophenoxy)phenyl]propionic acid (5.0 g) in benzene (30 ml), and refluxed under heating for 1.5 hours. The reaction mixture was evaporated, and toluene was added to the residue and then evaporated again. The crystalline residue (4.30 g) was recrystallized from a mixture of ethyl acetate and n-hexane to give 8-(2-chlorophenoxy)chroman-2-one (3.9 g). mp 123°-125° C.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 1.5 hours
  3. customThe reaction mixture was evaporated
  4. additiontoluene was added to the residue
  5. customevaporated again
  6. customThe crystalline residue (4.30 g) was recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-4e419dd5cde146a69931d44eb19cf35b
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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