2-Chloroethanol → HCID 12412279, compound

HRID 569604Notes

Reaction equation

HRID 569604 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[CH2:12][CH2:13][OH:14].[CH:15](O)=[O:16]>O>[CH:15]([O:14][CH2:13][CH2:12][O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:16]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 284Formic AcidHCID 46844-ChlorophenolHCID 14798Sodium Hydroxide

Product 1

HCID 12412279HCID 12412279, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-Chlorophenol (112 g) was added to a solution of sodium hydroxide (40 g) in water (100 ml). The mixture was heated to reflux, and 2-chloroethanol (80 g) was added dropwise with stirring. After cooling to room temperature, the mixture was extracted with ether. The organic phase was dried and evaporated to leave a residue which was refluxed with formic acid (150 ml) for 1 hour followed by distillation in vacuo. The product had boiling point 138°-40° C./1 mm Hg.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. extractionthe mixture was extracted with ether
  4. customThe organic phase was dried
  5. customevaporated
  6. customto leave a residue which
  7. distillationfollowed by distillation in vacuo

Sources & evidence

ORD record
ord-ad12b3d2025144a897b0a1b279f568fb
Source dataset
uspto-grants-1988_03
Patent number
US04732998

Reaction notes

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