Thionyl Chloride → 1,2,3,4-Tetrahydronaphthalene-2-carbonyl chloride

HRID 1942351Notes

Reaction equation

HRID 1942351 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11]([OH:13])=O.S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11]([Cl:16])=[O:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1013701,2,3,4-Tetrahydro-2-naphthoic acid

Product 1

HCID 156707901,2,3,4-Tetrahydronaphthalene-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

6.5 mmol (1.15 g) 1,2,3,4-Tetrahydro-naphthalene-2-carboxylic acid is dissolved in 20 mL toluene, 20 mL of thionylchloride are added, the mixture is heated to 60° C. in an oil bath for 2 hours. Then the mixture is concentrated in vacuum. Toluene is added to the residue and evaporated again. The crude product is obtained in almost quantitative yield.

Workup

  1. concentrationThen the mixture is concentrated in vacuum
  2. additionToluene is added to the residue
  3. customevaporated again

Sources & evidence

ORD record
ord-1a5a32472c094ced928c1d5034a3a950
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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