Chloroacetic Acid → Octadecyl chloroacetate

HRID 217545Notes

Reaction equation

HRID 217545 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Cl:20][CH2:21][C:22](O)=[O:23].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.C(OCC)C>[Cl:20][CH2:21][C:22]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:23]

Participants

6

Reactant 3

HCID 300Chloroacetic AcidHCID 1118Sulfuric AcidHCID 8221Stearyl Alcohol

Product 1

HCID 79299Octadecyl chloroacetate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-octadecanol 5 (5 0 g, 180 mmol), chloroacetic acid (17.5 g, 180 mmol) and concentrated sulfuric acid (0.1 mL) in 350 mL of toluene was refluxed overnight in a flask equipped with a Dean-Stark trap. The solution was diluted with 500 mL of diethyl ether and extracted twice with a saturated bicarbonate solution (500 mL). The aqueous phase was subsequently extracted with 400 mL of diethyl ether. The combined organic layers were dried with sodium sulfate and evaporated in vacuo yielding a brown solid, which was used without further purification. 1H-NMR (CDCl3) δ=4.20 (t, 2H), 4.07 (s, 2H), 1.68 (q, 2H), 1.30 (m, 30H), 0.89 (t, 3H) ppm. FT-IR: ν=2919, 2851, 1749 (C═O stretch), 1333, 1208 (C—O stretch), 786 cm−1.

Workup

  1. customequipped with a Dean-Stark trap
  2. extractionextracted twice with a saturated bicarbonate solution (500 mL)
  3. extractionThe aqueous phase was subsequently extracted with 400 mL of diethyl ether
  4. dry with materialThe combined organic layers were dried with sodium sulfate
  5. customevaporated in vacuo
  6. customyielding a brown solid, which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-e3980296798c4f669063bf3308642180
Source dataset
uspto-grants-2012_06
Patent number
US08197589B2

Reaction notes

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