Glycerol → HCID 20364920, compound

HRID 1679001Notes

Reaction equation

HRID 1679001 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[OH:10][CH2:11][CH:12]([CH2:14]O)[OH:13].O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:13][CH:12]1[CH2:11][O:10][CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=2)[O:6][CH2:14]1

Participants

6

Reactant 3

HCID 753GlycerolHCID 962WaterHCID 114773-Chlorobenzaldehyde

Product 1

HCID 20364920HCID 20364920, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 3-chlorobenzaldehyde (28.1 g, 0.2 mole), glycerol (18.4 g, 0.2 mole) and p-toluenesulfonic acid (0.1 g) in 150 ml of benzene was heated at reflux under a Dean-Stark apparatus until water was no longer collecting (3.6 ml). The solution was cooled, washed with 2% sodium bicarbonate solution (2 × 100 ml) and with water (2 × 100 ml). The washed solution was dried over magnesium sulfate and concentrated under reduced pressure. The oil remaining was distilled to give 18.1 g of colorless liquid which distilled at a pot temperature of 124°-128° C under 1 × 10-4 mm.

Workup

  1. temperaturewas heated
  2. customwas no longer collecting (3.6 ml)
  3. temperatureThe solution was cooled
  4. washwashed with 2% sodium bicarbonate solution (2 × 100 ml) and with water (2 × 100 ml)
  5. dry with materialThe washed solution was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. distillationThe oil remaining was distilled

Sources & evidence

ORD record
ord-16f6be91459c4430a3651aa4b3a67d9d
Source dataset
uspto-grants-1978_03
Patent number
US04077982

Reaction notes

Loading…