3-Hydroxybenzaldehyde → 3-(3-Chloro-2-hydroxypropoxy)benzaldehyde

HRID 648181Notes

Reaction equation

HRID 648181 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH2:10]([CH:12]1[O:14][CH2:13]1)[Cl:11]>N1C=CC=CC=1>[Cl:11][CH2:10][CH:12]([OH:14])[CH2:13][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 7835Epichlorohydrin

Product 1

HCID 128784723-(3-Chloro-2-hydroxypropoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-hydroxybenzaldehyde (24.4 g, 0.2 mol), epichlorohydrin (47 ml) and pyridine (0.4 ml) is heated 5 hours on a steam bath. The crude mixture is partitioned between methylenechloride-water and the CH2Cl2 extract washed with dilute aqueous NaHCO3, dried (Na2SO4), filtered and concentrated in vacuo to give the crude title product. Distillation gives a colorless oil bp 160° (0.2 mm); 21.2 g.

Workup

  1. temperatureis heated 5 hours on a steam bath
  2. customThe crude mixture is partitioned between methylenechloride-water
  3. extractionthe CH2Cl2 extract
  4. washwashed with dilute aqueous NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude title product
  9. distillationDistillation

Sources & evidence

ORD record
ord-228ebbddc8eb438a96c0fc17d988e7ed
Source dataset
uspto-grants-1983_10
Patent number
US04411899

Reaction notes

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