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

HRID 2057590Notes

Reaction equation

HRID 2057590 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 2

HCID 996PhenolHCID 7835Epichlorohydrin

Product 1

HCID 943001-Chloro-3-phenoxy-2-propanolYield 62.5%

Reagents, catalysts & solvents 1

HCID 2723721Piperidine, hydrochloride (1:1)Catalyst

Procedure

A mixture of phenol (94 g; 1.0 mole) and epichlorhydrin (138.8 g; 1.5 mole) was vigorously stirred at 100° C. in the presence of piperidine hydrochloride (2.0 g) for 6 hours, cooled, and the excess epichlorohydrin 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 116.4 g (62.5%) of 1-chloro-3-phenoxy-2-propanol of bp0.6 112° as a GLC pure material, νmax (film) 3310, 1603, 1590, 1495, 1245 cm-1 ; τ(CDCl3); 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 epichlorohydrin 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-8f33fa1f14a94f22afb954ae39de0a75
Source dataset
uspto-grants-1980_07
Patent number
US04211791

Reaction notes

Loading…