p-Toluenesulfonic acid → HCID 13203356, compound

HRID 2058800Notes

Reaction equation

HRID 2058800 reaction equation
[CH3:1][CH2:2][CH2:3][C:4](=O)[CH:5]([CH2:7][CH2:8][CH3:9])O.[CH2:11]([SH:16])[CH:12]([SH:15])[CH2:13][CH3:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:13]([CH:12]1[CH2:11][S:16][C:4]([CH2:3][CH2:2][CH3:1])=[C:5]([CH2:7][CH2:8][CH3:9])[S:15]1)[CH3:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 61829Butane-1,2-dithiolHCID 2197945-Hydroxyoctan-4-one

Product 1

HCID 13203356HCID 13203356, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Butyroin (12.2 g), butane-1,2-dithiol (14.4 g) and p-toluenesulfonic acid (0.5 g) were dissolved in toluene (50 g) and the solution refluxed under a Dean-Stark trap. It was worked up as in Example 3 to give 2-ethyl-2,3-dihydro-5,6-dipropyl-1,4-dithiin as a clear greenish liquid, boiling range 92°-105°/0.025 mm, yield 8.5 g (44%). NMR(CDCl3), 0.78-1.14 δ (overlapping triplets), 1.21-1.80 δ (multiplet) 2.07-2.37 δ (complex quartet), 2.6-3.4 δ (multiplet).

Workup

  1. temperaturethe solution refluxed under a Dean-Stark trap

Sources & evidence

ORD record
ord-825519268a4f44b19c0c0b6359dce350
Source dataset
uspto-grants-1982_03
Patent number
US04319033

Reaction notes

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