Sodium Hydroxide → HCID 117873508, compound

HRID 64495Notes

Reaction equation

HRID 64495 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]Cl)([CH3:4])([CH3:3])[CH3:2].NC(N)=[S:15].[OH-].[Na+]>O>[C:1]([O:5][CH:6]([SH:15])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 132806981-tert-Butoxy-6-chlorohexane

Product 1

HCID 117873508HCID 117873508, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

After 73.2 g of 1-tert-butoxy-6-chlorohexane (0.38 mol), 38 g of thiourea (0.5 mol), and 30 ml of distilled water were put into a 500 ml two-necked flask equipped with a condenser and refluxed at 120° C. for 5 hours, a temperature was cooled to room temperature, and 300 ml of a previously prepared aqueous solution of NaOH (30 g) was added thereto and refluxed at 110° C. for 14 hours. The reactant was cooled to room temperature, the formed organic layer was extracted with ether and dried over MgSO4, and then the solvent was removed under reduced pressure, thereby obtaining 55.6 g of an oily product (6-tert-butoxyhexane-1-thiol, yield 76.9 mol %). Purity of the product confirmed through gas chromatography (GC) analysis was 97%, and results of proton nuclear magnetic resonance (1H-NMR) spectroscopy were as follows.

Workup

  1. customequipped with a condenser
  2. temperaturea temperature was cooled to room temperature
  3. temperaturerefluxed at 110° C. for 14 hours
  4. temperatureThe reactant was cooled to room temperature
  5. extractionthe formed organic layer was extracted with ether
  6. dry with materialdried over MgSO4
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d3e03ff8f8ed413a8cc89a801345663d
Source dataset
uspto-grants-2016_09
Patent number
US09447211B2

Reaction notes

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