Phenol → 1-Chloro-3-phenoxy-2-propanol

HRID 2163710Notes

Reaction equation

HRID 2163710 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([CH:10]1[O:12][CH2:11]1)[Cl:9].Cl.N1CCCCC1>>[Cl:9][CH2:8][CH:10]([OH:12])[CH2:11][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 7835EpichlorohydrinHCID 2723721Piperidine, hydrochloride (1:1)

Product 1

HCID 943001-Chloro-3-phenoxy-2-propanol

Procedure

A mixture of phenol (94g; 1.0 mole) and epichlorhydrin (138.8g; 1.5 mole) was vigorously stirred at 100° C. in the presence of piperidine hydrochloride (2.0g) for 6 hours, cooled, and the excess epichlorhydrin removed at 100° in vacuo. The residue was cooled, dissolved in an equal volume of chloroform and stirred vigorously with excess concentrated hydrochloric acid for 0.5 hours. After separatiin of the phases the organic layer was washed with water, dried and evaporated to a colourless oil. Distillation gave 116.4g (62.5%) of 1-chloro-3-phenoxy-2-propanol of bp0.6 112° as a GLC pure material, νmax (film) 3310, 1603, 1590, 1495, 1245cm-1 ; τ(CDCl3); 7.40 (broad exchangeable s); 6.25 (2H, d, J 3.5Hz); 5.90 (2H, s); 5.90 (1H, m); 3.21-2.56 (5H,m).

Workup

  1. temperaturecooled
  2. customthe excess epichlorhydrin removed at 100° in vacuo
  3. temperatureThe residue was cooled
  4. dissolutiondissolved in an equal volume of chloroform
  5. washAfter separatiin of the phases the organic layer was washed with water
  6. customdried
  7. customevaporated to a colourless oil
  8. distillationDistillation

Sources & evidence

ORD record
ord-e90ef48ff3ae4383be47217d9334f113
Source dataset
uspto-grants-1979_01
Patent number
US04136192

Reaction notes

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