Thionyl Chloride → 5,6,7,8-Tetrahydronaphthalene-1-carbonyl chloride

HRID 2185873Notes

Reaction equation

HRID 2185873 reaction equation
[C:1]1([C:11]([OH:13])=O)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O>>[C:1]1([C:11]([Cl:16])=[O:13])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2396045,6,7,8-Tetrahydro-1-naphthalenecarboxylic acid

Product 1

HCID 27531625,6,7,8-Tetrahydronaphthalene-1-carbonyl chloride

Procedure

A solution of 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (J. W, Burnham, W. P. Duncan, E. J. Eisenbaum, G. W. Keen, M. C. Hamming, Org. Prep. Proc. Int. 285-290 (1973))(0.205 g, 1.16 mmol) in thionyl chloride (3.26 g, 27.42 minol) was heated at 80 ° C. for 3 h under a stream of nitrogen. Excess thionyl chloride was removed in vacuo, and the residue concentrated a second time from toluene to afford 5,6,7,8 tetrahydo-1-naphthalenecarbonyl chloride as a brown oil. The residue was dissolved in dry CH2Cl2 and used without further purification.

Workup

  1. customExcess thionyl chloride was removed in vacuo
  2. concentrationthe residue concentrated a second time from toluene

Sources & evidence

ORD record
ord-1ad2521734224eaeb9ef929379fd08ce
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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