Chloroacetic Acid → HCID 18667853, compound

HRID 384569Notes

Reaction equation

HRID 384569 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[Cl:7][CH2:8][C:9]([OH:11])=O>C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:7][CH2:8][C:9]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][O:6][C:9](=[O:11])[CH2:8][Cl:7])=[O:11]

Participants

4

Reactant 2

HCID 300Chloroacetic AcidHCID 80641,4-Butanediol

Product 1

HCID 18667853HCID 18667853, compound

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidSolvent

Procedure

In a 2 liter, 4 neck round bottom flask equipped with a mechanical stirrer, a solution of 75 grams of 1,4-butanediol, 240 grams of chloroacetic acid and 3 grams of para-toluenesulphonic acid 750 ml toluene was refluxed for 6 hours using a Dean-Stark apparatus. The solution was then cooled to room temperature. The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml), water (2×300 ml), dried over sodium sulfate, and distilled to get crude 21, which was purified by recrystallization in chloroform:hexane (1:7) to get 92 grams of pure 21 as a white fluffy powder. m.p: 74-76.5° C., 1H NMR (CDCl3) δ 1.78 (t, 2H, CH2), 4.05 (s, 2H, CH2), 4.25 (t, 2H, CH2)

Workup

  1. customIn a 2 liter, 4 neck round bottom flask equipped with a mechanical stirrer
  2. washThe toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml), water (2×300 ml)
  3. dry with materialdried over sodium sulfate
  4. distillationdistilled
  5. customto get crude 21, which
  6. customwas purified by recrystallization in chloroform:hexane (1:7)
  7. customto get 92 grams of pure 21 as a white fluffy powder

Sources & evidence

ORD record
ord-d51246eff89b4459971b90419f5e142b
Source dataset
uspto-grants-2013_02
Patent number
US08367747B2

Reaction notes

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