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

HRID 1706454Notes

Reaction equation

HRID 1706454 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 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 116.4 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 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-9ffca8f774504449bb8aee984e2b00d3
Source dataset
uspto-grants-1980_06
Patent number
US04207335

Reaction notes

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