Ethyl formate → Ethyl 2-formylhexanoate

HRID 1445308Notes

Reaction equation

HRID 1445308 reaction equation
[H-].[Na+].[C:3]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH:13](OCC)=[O:14]>C1COCC1>[CH:13]([CH:4]([CH2:5][CH2:6][CH2:7][CH3:8])[C:3]([O:10][CH2:11][CH3:12])=[O:9])=[O:14]

Participants

5

Reactant 3

HCID 8025Ethyl formate2×HCID 24758Sodium hydride2×HCID 31265Ethyl hexanoate

Product 1

HCID 12592620Ethyl 2-formylhexanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

First, 60 g of 60% NaH was suspended in 600 ml of THF and 72.1 g of ethyl hexanoate was added dropwise to the suspension solution thus prepared at room temperature. After the suspension solution was raised in temperature to 40° C. and stirred for 15 minutes, 185.2 g of ethyl formate was added dropwise for 6 hours. Furthermore, 30 g of 60% NaH and 92.6 g of ethyl formate were divided into four parts and each part was added separately. Afterward, the solution mixture was stirred at 40° C. for 3 hours.

Workup

  1. customthus prepared at room temperature
  2. additioneach part was added separately
  3. stirringAfterward, the solution mixture was stirred at 40° C. for 3 hours

Sources & evidence

ORD record
ord-37c63928fb0c40079ba789c8b12c74af
Source dataset
uspto-grants-2010_02
Patent number
US07666659B2

Reaction notes

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