Decanoic Acid → Chloromethyl decanoate

HRID 411771

Reaction equation

HRID 411771 reaction equation
[C:1]([OH:12])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C([O-])(O)=O.[Na+].[Cl:18][CH2:19]OS(Cl)(=O)=O.C(Cl)Cl>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.O>[Cl:18][CH2:19][O:11][C:1](=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 2969Decanoic AcidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 2733556Chloromethyl chlorosulfate

Product 1

HCID 572571Chloromethyl decanoateYield 100%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Decanoic acid (0.2 gm, 1.2 mmol) was treated with 4 eq NaHCO3, 0.1 eq Bu4NHSO4 and, 1.2 eq ClCH2OSO2Cl in 1:1 CH2Cl2:H2O. The reaction was stirred vigorously at 0° C. for 30 min then room temperature (“RT”) for 3 hrs. Aqueous workup yielded chloromethyldecanoate (yield 100%).

Workup

  1. waitroom temperature (“RT”) for 3 hrs

Sources & evidence

ORD record
ord-01ffc514e7334937b06f28c9c7eef12f
Source dataset
uspto-grants-2003_05
Patent number
US06559164B1

Linked notes

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