Thionyl Chloride → beta-(9,10-Dihydro-9,10-methano-9-anthryl)propionic acid chloride

HRID 27951Notes

Reaction equation

HRID 27951 reaction equation
[CH:1]1[C:14]2[C:13]3([CH2:16][CH2:17][C:18]([OH:20])=O)[CH2:15][CH:6]([C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:23])=O>C1C=CC=CC=1>[CH:1]1[C:14]2[C:13]3([CH2:16][CH2:17][C:18]([Cl:23])=[O:20])[CH2:15][CH:6]([C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12507124HCID 12507124, compound

Product 1

HCID 54077621beta-(9,10-Dihydro-9,10-methano-9-anthryl)propionic acid chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of β-(9,10-dihydro-9,10-methano-9-anthryl)propionic acid and thionyl chloride in benzene was refluxed for 4 hours. Evaporation of excess thionyl chloride and benzene gave β-(9,10-dihydro-9,10-methano-9-anthryl)-propionic acid chloride, which was dissolved in dry tetrahydrofuran. The solution was added to a 30% aqueous monomethylamine solution at 0°-5° C. The reaction mixture was stirred at 0°-15° C., diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to give β-(9,10-dihydro-9,10-methano-9-anthryl)-propionic acid monomethylamide. M.P. 200°-201° C.

Workup

  1. customEvaporation of excess thionyl chloride and benzene

Sources & evidence

ORD record
ord-a31659226e07447bbf1070f7152fe3b7
Source dataset
uspto-grants-1980_09
Patent number
US04224344

Reaction notes

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