p-Toluenesulfonic acid → 2,3-Dihexyl-5,6-dihydro-5-methyl-1,4-dithiin

HRID 2058803Notes

Reaction equation

HRID 2058803 reaction equation
O[CH:2]([C:9](=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:17]([SH:21])[CH:18]([SH:20])[CH3:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:3]([C:2]1[S:21][CH2:17][CH:18]([CH3:19])[S:20][C:9]=1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 612172,3-DimercaptopropaneHCID 866818-Hydroxytetradecan-7-one

Product 1

HCID 132033602,3-Dihexyl-5,6-dihydro-5-methyl-1,4-dithiinYield 63%

Procedure

The method of Example 4 was used, using 7-hydroxytetradecan-8-one (22.8 g), propane-1,2-dithiol (10.8 g) and p-toluenesulphonic acid (0.5 g) to give 2,3-dihexyl-5,6-dihydro-5-methyl-1,4-dithiin as a greenish oil, bp 148°-155°/0.2 mm, yield 63%. NMR, 0.7-1.8 δ (multiplets), 2.05-2.35 δ (broad triplet), 2.45-3.6 δ (multiplets), 2.95 δ (doublet).

Sources & evidence

ORD record
ord-fd9d90a68ada4906afc43623037239d3
Source dataset
uspto-grants-1982_03
Patent number
US04319033

Reaction notes

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