Chloroform → HCID 20329636, compound

HRID 2057970Notes

Reaction equation

HRID 2057970 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:15].[Na+].C(Cl)(Cl)Cl>C(O)C>[O:1]([C:8]1[C:9]2[CH:4]=[C:3]([C:2]([OH:1])=[O:15])[O:14][C:10]=2[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 128423-PhenoxyphenolHCID 14798Sodium Hydroxide

Product 1

HCID 20329636HCID 20329636, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

14.0 g of meta-phenoxyphenol was dissolved in 700 ml of 95% ethanol. 468 g of sodium hydroxide was then added rapidly. The resulting suspension was heated to 70°-80° C. Then 558.7 g of chloroform was added, at such a rate that gentle reflux was maintained; the addition required 10 hours. The mixture then was stirred for 2 hours at 75°-80° C., held at room temperature overnight and filtered. The solid product was dissolved in 1000 ml of water. The solution was acidified to pH=2 with concentrated hydrochloric acid, then was extracted with ether. The ether layer was dried (MgSO4) and concentrated. The residue was extracted with hot petroleum ether. The extract was dried (Na2SO4) and concentrated to give an oil, which was wet column chromatographed over silica gel, using first a 9/1 v/v mixture, then a 4/1 v/v mixture of petroleum ether and ether as eluent. The fourth fraction obtained, after removal of the solvents, was identified as 2-hydroxy-6-phenoxybenzaldehyde.

Workup

  1. temperatureThe resulting suspension was heated to 70°-80° C
  2. temperatureat such a rate that gentle reflux
  3. temperaturewas maintained
  4. additionthe addition required 10 hours
  5. waitheld at room temperature overnight
  6. filtrationfiltered
  7. dissolutionThe solid product was dissolved in 1000 ml of water
  8. extractionwas extracted with ether
  9. dry with materialThe ether layer was dried (MgSO4)
  10. concentrationconcentrated
  11. extractionThe residue was extracted with hot petroleum ether
  12. dry with materialThe extract was dried (Na2SO4)
  13. concentrationconcentrated
  14. customto give an oil, which
  15. customchromatographed over silica gel
  16. additiona 4/1 v/v mixture of petroleum ether and ether as eluent
  17. customThe fourth fraction obtained
  18. customafter removal of the solvents

Sources & evidence

ORD record
ord-e050372a7549498b992a888226c507f6
Source dataset
uspto-grants-1980_07
Patent number
US04213998

Reaction notes

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