4-Toluenesulfonyl chloride → HCID 13034294, compound

HRID 1030255Notes

Reaction equation

HRID 1030255 reaction equation
[O:1]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH2:13][OH:14].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21]([O:14][CH2:13][CH:2]2[CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:1]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 273308575507-26-5

Product 1

HCID 13034294HCID 13034294, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Reaction in pyridine (13 ml) of 1,4,7,10-tetraoxacyclo-dodecane-2-methanol (5 g) with p-toluenesulphonyl chloride (5 g) produces 1,4,7,10-tetraoxacyclododecane-2-methanol p-toluenesulphonate (8 g; m.p. 49°-51° C. from diethyl ether). Subsequent reaction with diethyl malonate (3.36 ml) and potassium tert-butoxide (3.47 g) in N-methyl pyrrolidone (30 ml) yields [(1,4,7,10-tetraoxacyclododecane-2-yl)methyl]-malonate diethyl ester as a viscous oil that is treated with aqueous lithium hydroxide 0.8 g) to obtain pure [(1,4,7,10-tetraoxacyclododecane-2-yl)methyl]-malonic acid N.M.R. (CDCl3): 2.08-2.19; 3.48-3.82; 9.38].

Sources & evidence

ORD record
ord-13ea4726f31f44688fe24e7de5c1c12f
Source dataset
uspto-grants-1992_04
Patent number
US05104895

Reaction notes

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