Chloroacetic Acid → Dodecyl chloroacetate

HRID 1802995Notes

Reaction equation

HRID 1802995 reaction equation
[CH2:1]([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Cl:14][CH2:15][C:16](O)=[O:17].S(=O)(=O)(O)O>C1C=CC=CC=1>[Cl:14][CH2:15][C:16]([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:17]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 1118Sulfuric AcidHCID 81931-Dodecanol

Product 1

HCID 228182Dodecyl chloroacetateYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The mixture of 1-dodecanol (0.2 mol, 37.27 g), chloroacetic acid (0.2 mol, 18.9 g), benzene (200 ml) and sulfuric acid (2 ml) was refluxed for 12 hrs. After the reaction, the mixture was washed with 25% Na2CO3 (100 ml). The organic layer was dried with magnesium sulfate and then evaporated, the remaining liquid was distilled under vacuum to provide a colorless oil (bp 150° C./3 mmHg) in 90% yield.

Workup

  1. temperaturewas refluxed for 12 hrs
  2. customAfter the reaction
  3. washthe mixture was washed with 25% Na2CO3 (100 ml)
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. customevaporated
  6. distillationthe remaining liquid was distilled under vacuum
  7. customto provide a colorless oil (bp 150° C./3 mmHg) in 90% yield

Sources & evidence

ORD record
ord-4b18f84f11144ef7944a5d481f27d3d6
Source dataset
uspto-grants-2013_01
Patent number
US08349966B2

Reaction notes

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