Decanal → HCID 12625795, compound

HRID 1076870Notes

Reaction equation

HRID 1076870 reaction equation
[CH:1](=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].S(Cl)([Cl:15])(=O)=O>C(Cl)Cl>[Cl:15][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:1]=[O:11]

Participants

4

Reactant 2

HCID 8175DecanalHCID 24648Sulfuryl chloride

Product 1

HCID 12625795HCID 12625795, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 59 g of caprinaldehyde, 15 ml of methylene chloride and 52 g of sulfuryl chloride was stirred for 2 hours, refluxed for 1 hour and was then rectified to obtain 34.5 g of α-chlorocaprinaldehyde with a boiling point of 115°C at 12 mm Hg and a refractive index of nD27 = 1.4460. A mixture of 11.6 g of the said product, 10 g of ethyl γ-propargyl-β -ethoxy-crotonate and 42.2 ml of butyl lithium were reacted as in Step A of Example 2 to obtain 4.75 g of ethyl 3-oxo-8-hydroxy-9-chloro-6-heptadecynoate with a refractive index of nD22 = 1.4780.

Workup

  1. temperaturerefluxed for 1 hour

Sources & evidence

ORD record
ord-03d20aedbac541bfbfa6fcaa575225fa
Source dataset
uspto-grants-1976_05
Patent number
US03958005

Reaction notes

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