HCID 71294272, compound → Ethyl Dodecanoate

HRID 1398064Notes

Reaction equation

HRID 1398064 reaction equation
[CH3:1][CH:2]1O[CH:5]([CH2:7][CH2:8][C:9](=O)[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:4][CH2:3]1.[H][H]>O>[C:13]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

4

Reactant 2

HCID 71294272HCID 71294272, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 7800Ethyl Dodecanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Neat ethyl 7-(5-methyltetrahydrofuran-2-yl)-5-oxoheptanoate was flowed at a pressure of 470 psig, and temperature of 240° C. under flowing hydrogen gas for 28 hours. The liquid flow rate and hydrogen gas flow rates were kept constant relative to each other, e.g. 0.03 mL/min liquid flow and 30 mL/min gas flow; 0.06 and 60 mL/min; or 0.09 and 90 mL/min The effluent was primarily organic with a small spontaneously separating water layer beneath the organic phase. Not counting the startup and shutdown, 62.9 g of organic phase was collected out of a theoretical 68.5 g, or 91.9%. GCMS analysis revealed an initial high concentration of 58.2% ethyl dodecanoate, 28.7% dodecanoic acid, and 13% intermediates, possibly ethyl 7-(5-methyltetrahydrofuran-2-yl)heptanoate.

Workup

  1. customwas collected out of a theoretical 68.5 g, or 91.9%

Sources & evidence

ORD record
ord-d46ff575766d4f2eba2681f553b55f14
Source dataset
uspto-grants-2014_12
Patent number
US08901329B2

Reaction notes

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