Chloroform → Dodecyl chloroacetate

HRID 1111423Notes

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[C:15](OCCl)=[O:16].C(N(CC)CC)C.[CH:27]([Cl:30])(Cl)Cl>>[Cl:30][CH2:27][C:15]([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:16]

Participants

Reactant 4

HCID 6212Chloroform

HCID 81931-Dodecanol

HCID 8471Triethylamine

HCID 62754Chloromethyl chloroformate

Product 1

HCID 228182Dodecyl chloroacetateYield 94%

Procedure

A mixture of dodecanol (10 g, 0.054 mol), chloromethyl chloroformate (6 g, 0.05 mol) and triethylamine (5.5 g) in 40 ml of dry chloroform was stirred at room temperature for 16 hours. The reaction mixture was then washed twice with water (50 ml per washing) and the organic phase was dried over anhydrous magnesium sulfate. Removal of the solvent gave 13.3 g (94% yield) of liquid product, which was chromatographed through a column of Florisil using chloroform as the eluent. 1HNMR(CCl4) δ0.90(3H, t, CH3); 1.28[20 H, s, broad, --(CH2)10 --]; 3.93(2H, s, --CH2Cl); 4.11 (2H, t, J=6Hz, --CH2 --O). νmax (film): 2940, 2880(CH); 1765, 1745(C=O); 1180 (--C--O--C--)cm-1.

Workup

washThe reaction mixture was then washed twice with water (50 ml per washing)
dry with materialthe organic phase was dried over anhydrous magnesium sulfate
customRemoval of the solvent

Sources & evidence

ORD record: ord-3fff0360b6094341bb11a17d55ee23b8
Source dataset: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04980378

Reaction notes

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