Chlorine → HCID 18687365, compound

HRID 1872697Notes

Reaction equation

HRID 1872697 reaction equation
[Cl:1]Cl.[CH2:3]([O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[C:13]([O:21][CH3:22])[CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)(=O)C>[CH2:3]([O:10][C:11]1[C:20]([Cl:1])=[CH:19][C:14]([C:15]([OH:17])=[O:16])=[C:13]([O:21][CH3:22])[CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 108260394-Benzyloxy-2-methoxybenzoic acid methyl ester

Product 1

HCID 18687365HCID 18687365, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
22.5 °C

Procedure

A solution of chlorine (5.1 g) in acetic acid (100 ml) was added dropwise to a solution of methyl 4-benzyloxy-2-methoxybenzoate (10 g) in acetic acid (40 ml) whilst maintaining the temperature at 20-25° C. The mixture was poured into ice-water and extracted with dichloromethane. The organic extract was dried over sodium sulfate and concentrated in vacuo. The resulting crude material was suspended in ethanol (500 ml) and treated with 10% aqueous sodium hydroxide (16 ml). The mixture was heated at reflux overnight and then concentrated in vacuo. The residue was treated with excess 5M HCl and extracted into dichloromethane. The extract was dried (sodium sulfate) and concentrated in vacuo to afford a white solid which was crystallised from ethanol to give the title compound (6.3 g).

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. additiontreated with 10% aqueous sodium hydroxide (16 ml)
  6. temperatureThe mixture was heated
  7. temperatureat reflux overnight
  8. concentrationconcentrated in vacuo
  9. additionThe residue was treated with excess 5M HCl
  10. extractionextracted into dichloromethane
  11. dry with materialThe extract was dried (sodium sulfate)
  12. concentrationconcentrated in vacuo
  13. customto afford a white solid which
  14. customwas crystallised from ethanol

Sources & evidence

ORD record
ord-d068763b7ba94c94bd7394f3e5164fc3
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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