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

HRID 2050158Notes

Reaction equation

HRID 2050158 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 separation 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(CSCl3); 7.40 (broad exchangeable s); 6.25 (2H, d, J 3.5 Hz); 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. customAfter separation of the phases the organic layer
  6. washwas washed with water
  7. customdried
  8. customevaporated to a colourless oil
  9. distillationDistillation

Sources & evidence

ORD record
ord-303f573a7d3e46b68c2588bc267d44c3
Source dataset
uspto-grants-1980_04
Patent number
US04200577

Reaction notes

Loading…