Thionyl Chloride → HCID 20471696, compound

HRID 1388147Notes

Reaction equation

O[CH2:2][CH:3]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.S(Cl)([Cl:16])=O>>[Cl:16][CH2:2][CH:3]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 122404Cycloundecanemethanol

Product 1

HCID 20471696HCID 20471696, compound

Procedure

The starting material 3-cycloundecylpropan-1-ol is obtained as follows: hydroxymethylcycloundecane is reacted with thionyl chloride to give chloromethylcycloundecane, which is reacted with malonic acid diethyl ester in the presence of sodium ethylate to give (cycloundecylmethyl)-malonic acid diethyl ester, which, after saponifying the ester group and decarboxylating the corresponding malonic acid, gives 3-cycloundecylpropionic acid. 3-Cycloundecylpropionic acid is reduced with lithium aluminum hydride in tetrahydrofuran to give 3-cycloundecylpropanol.

Sources & evidence

ORD record: ord-6ceeb0e5580f4deb9986b3730290f021
Source dataset: uspto-grants-1984_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04430339

Reaction notes

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