1,2-Dichloroethane → Orcinol

HRID 2083688Notes

Reaction equation

HRID 2083688 reaction equation
Cl[CH2:2]CCl.[CH3:5][C:6]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][C:7]=1[OH:8]>CC1C=CC(O)=CC=1O>[CH3:2][C:10]1[CH:11]=[C:12]([OH:13])[CH:6]=[C:7]([CH:9]=1)[OH:8].[CH3:5][C:6]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][C:7]=1[OH:8]

Participants

5

Reactant 2

HCID 111,2-DichloroethaneHCID 118432-Methylresorcinol

Product 2

HCID 10436OrcinolHCID 118432-Methylresorcinol

Reagents, catalysts & solvents 1

HCID 103331,3-Benzenediol, 4-methyl-Solvent

Procedure

This product mixture is introduced into a separation vessel or series of separation vessels. This vessel or these vessels may be fractional distillation vessels. In these vessels, the mono-substituted methylresorcinol isomers are separated from unreacted resorcinol and other methylated hydroxyaromatic compounds. The boiling points of these compounds are substantially close to each other so that a good separation in a single fractional distillation vessel may be difficult. The boiling points are: m-methoxy phenol 244.3° C., 2-methylresorcinol 264° C., 4-methylresorcinol 267°-270° C., 5-methylresorcinol 287°-290° C., and resorcinol 275.9° C. and higher methylated resorcinols above 290° C. Preferably, the product mixture is fractionally distilled to obtain a fraction rich in 5-methylresorcinol and a fraction rich in 2-methylresorcinol. Also, a fraction rich in 4-methylresorcinol may be obtained. Each rich fraction is treated in a separate vessel to fractional crystallization from 1,2-dichloroethane with a varied solvent ratio. From this operation the appropriate mono-substituted resorcinol and preferably, predominantly the 5-methylresorcinol along with some 2-methylresorcinol are obtained in a pure state.

Workup

  1. additionThis product mixture is introduced into a separation vessel
  2. customseries of separation vessels
  3. customThis vessel or these vessels may be fractional
  4. distillationdistillation vessels
  5. customIn these vessels, the mono-substituted methylresorcinol isomers are separated from unreacted resorcinol and other methylated hydroxyaromatic compounds
  6. customThe boiling points of these compounds are substantially close to each
  7. customother so that a good separation in a single fractional distillation vessel
  8. customm-methoxy phenol 244.3° C., 2-methylresorcinol 264° C., 4-methylresorcinol 267°-270° C., 5-methylresorcinol 287°-290° C., and resorcinol 275.9° C. and higher methylated resorcinols above 290° C
  9. distillationPreferably, the product mixture is fractionally distilled
  10. customto obtain a fraction rich in 5-methylresorcinol

Sources & evidence

ORD record
ord-4776bedca25c4d6b85aa73fc32e9d362
Source dataset
uspto-grants-1978_04
Patent number
US04086281

Reaction notes

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