Phenol → HCID 12592541, compound

HRID 647560Notes

Reaction equation

HRID 647560 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)[Cl:2].[CH2:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[CH:7]=[CH2:8].C1(O)C=CC=CC=1>N1C=CC=CC=1>[CH2:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:4][CH:3]([OH:5])[CH2:1][Cl:2])[CH:7]=[CH2:8]

Participants

5

Reactant 3

HCID 996PhenolHCID 7835EpichlorohydrinHCID 156242-Allylphenol

Product 1

HCID 12592541HCID 12592541, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

In a flask are placed 92.5 g (1 mol) of epichlorohydrin, 33.5 g (0.25 mol) of o-allylphenol and 0.3 ml of pyridine is added. The mixture is taken to 80° C. in about 1 hour then the temperature is raised to 90° C. and maintained for about 6 hours until the phenol has disappeared completely. The mixture is then cooled and the excess of epichlorohydrin evaporated. The remaining oil is taken up in 100 ml chloroform and 50 ml of HCl (d415 -1.19) are slowly added. The organic phase is then washed two to three times in water then dried over Na2SO4. After evaporation of the chloroform, 56.6 g (yield: about 100%) are obtained of 1-(o-allylphenoxy)-3-chloro-2-propanol in the form of an oil, dark brown in colour.

Workup

  1. customIn a flask are placed
  2. temperatureThe mixture is then cooled
  3. customthe excess of epichlorohydrin evaporated
  4. addition50 ml of HCl (d415 -1.19) are slowly added
  5. washThe organic phase is then washed two to three times in water
  6. dry with materialthen dried over Na2SO4
  7. customAfter evaporation of the chloroform, 56.6 g (yield: about 100%)

Sources & evidence

ORD record
ord-4f10159ffe7f4d48a5dd381108474e97
Source dataset
uspto-grants-1983_10
Patent number
US04409242

Reaction notes

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