Thionyl Chloride → HCID 12882333, compound

HRID 1395370Notes

Reaction equation

HRID 1395370 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([C:16]([CH3:18])([CH3:17])[CH:15]2[C:19]([OH:21])=[O:20])[CH:7]=1.[O:22]([C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1.CCOCC>[Cl:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([C:16]([CH3:17])([CH3:18])[CH:15]2[C:19]([O:21][CH2:32][C:31]2[CH:34]=[CH:35][CH:36]=[C:29]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:30]=2)=[O:20])[CH:7]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 262953-Phenoxybenzyl alcoholHCID 13097323HCID 13097323, compound

Product 1

HCID 12882333HCID 12882333, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Pyridine (1.68 g) and thionyl chloride (2.5 g) are added to a mixture of 3'-chloro-3,3-dimethyl-spiro[cyclopropane-1,1'-indene]-2-carboxylic acid (5.0 g; 0.02 mole) and ether (50 ml). After two hours at room temperature, pyridine (1.68 g) and m-phenoxybenzyl alcohol (4.0 g) are added and the reaction mixture stirred at room temperature overnight. The reaction mixture is then washed with water, the ether fraction dried over magnesium sulfate and evaporated to dryness. The residue is purified on a dry column (silica gel; 20% methylene chloride:hexane) to afford 3.0 g of title compound, a yellow-orange liquid. The sample is 90-95% pure by NMR, and shows an ester carbonyl stretch at 1730 cm-1 in IR.

Workup

  1. washThe reaction mixture is then washed with water
  2. dry with materialthe ether fraction dried over magnesium sulfate
  3. customevaporated to dryness
  4. customThe residue is purified on a dry column (silica gel; 20% methylene chloride:hexane)

Sources & evidence

ORD record
ord-fc3f92d7dded4d2b9e5d4ef3cdcdabd2
Source dataset
uspto-grants-1980_05
Patent number
US04203918

Reaction notes

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