Propyl mercaptan → HCID 21569152, compound

HRID 1579691Notes

Reaction equation

HRID 1579691 reaction equation
[CH3:1][C:2](=[O:8])/[CH:3]=[CH:4]\[C:5](=[O:7])[CH3:6].[CH2:9]([SH:12])[CH2:10][CH3:11].N1CCCCC1>N1CCCCC1.CCOCC>[CH2:9]([S:12][CH:4]([CH2:3][C:2](=[O:8])[CH3:1])[C:5](=[O:7])[CH3:6])[CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 7848Propyl mercaptanHCID 8082PiperidineHCID 535448517559-81-8

Product 1

HCID 21569152HCID 21569152, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 3283Diethyl EtherSolvent

Procedure

In a 500 ml flask fitted with thermometer, addition funnel, reflux condenser and magnetic stirrer are placed 95 ml of ether, 35.4 g of cis-3-hexene-2,5-dione and one drop of piperidine. Addition of 24 g of n-propanethiol is started and as the addition progresses more piperidine is added (33 drops total) periodically. After standing 18 hours, the solution is washed successively with two 7.5 ml portions of 10% hydrochloric acid, saturated sodium chloride solution (10 ml), 5% sodium bicarbonate solution and two 10 ml portions of saturated sodium chloride solution. The ether solution is dried over sodium sulfate and concentrated to give 51.4 g of a dark yellow oil. Analysis by GLC shows the material to be essentially pure 3-thiopropyl-2,5-hexanedione. Mass spectral analysis shows molecular ion 188 then descending order 43, 103, 41, 145, 71, 114 and 61 m/e units.

Workup

  1. customIn a 500 ml flask fitted with thermometer, addition funnel
  2. temperaturereflux condenser and magnetic stirrer
  3. additionis started and as the addition
  4. additionis added (33 drops total) periodically
  5. washthe solution is washed successively with two 7.5 ml portions of 10% hydrochloric acid, saturated sodium chloride solution (10 ml), 5% sodium bicarbonate solution and two 10 ml portions of saturated sodium chloride solution
  6. dry with materialThe ether solution is dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c2913a3f9443424b847a6989f09e837b
Source dataset
uspto-grants-1976_01
Patent number
US03931270

Reaction notes

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