Guaiacol → 4-Chloro-1-(2-methoxyphenoxy)-2-butanol

HRID 1639059Notes

Reaction equation

HRID 1639059 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[OH-].[Na+].O.Cl[CH2:14][CH:15]([OH:19])[CH2:16][CH2:17][Cl:18]>C(O)(C)C>[Cl:18][CH2:17][CH2:16][CH:15]([OH:19])[CH2:14][O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 460GuaiacolHCID 962WaterHCID 14798Sodium HydroxideHCID 170211,4-Dichloro-2-butanol

Product 1

HCID 131203504-Chloro-1-(2-methoxyphenoxy)-2-butanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 2 moles (248.26 g) of 2-methoxyphenol, 4 moles (160 g) of sodium hydroxide, 250 ml of water and 1 liter of isopropanol was added with stirring 2.2 moles (314.64 g) of 1,4-dichloro-2-butanol. The mixture was refluxed gently overnight. The reaction mixture was extracted with 1 liter of isopropyl ether, dried over sodium sulfate and distilled under reduced pressure. The distillate which was collected at 136°-138° C./0.015 mm (395.8 g) solidified to a white crystalline solid which melted at 48°-50° C.

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed gently overnight
  3. extractionThe reaction mixture was extracted with 1 liter of isopropyl ether
  4. dry with materialdried over sodium sulfate
  5. distillationdistilled under reduced pressure
  6. distillationThe distillate which was collected at 136°-138° C./0.015 mm (395.8 g)

Sources & evidence

ORD record
ord-a493c75d6e7d4f3bbf34b2b4fb6d12de
Source dataset
uspto-grants-1989_11
Patent number
US04882330

Reaction notes

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