Cyclohexaneacetaldehyde, alpha-methyl- → HCID 18931636, compound

HRID 64506Notes

Reaction equation

HRID 64506 reaction equation
C1(C(C)C=O)CCCCC1.[C:11]([C:13](=[CH:19][CH:20]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH3:21])C(OCC)=O)#[N:12]>>[CH:22]1([CH:20]([CH3:21])[CH2:19][CH2:13][C:11]#[N:12])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 95560Cyclohexaneacetaldehyde, alpha-methyl-HCID 123918932Ethyl 2-cyano-4-cyclohexylpenta-2-enoate

Product 1

HCID 18931636HCID 18931636, compound

Procedure

In a 2 L flask with a distillation tube attached thereto, 475 g of ethyl cyanoacetate (VI-1) (4.20 moles, 1.05 times by mole with respect to the 2-cyclohexylpropanal (II)), 6.0 g of acetic acid (0.10 millimole, 0.025 times by mole with respect to the 2-cyclohexylpropanal (II)), and 3.4 g of piperidine (40 millimoles, 0.01 times by mole with respect to the 2-cyclohexylpropanal (II)) were placed, which then was stirred at room temperature. Then, 561 g (4.00 moles) of 2-cyclohexylpropanal (II) (“Pollenal II” (Trade Name), manufactured by Kao Corporation) was dropped thereinto over 40 minutes. Thereafter, this was heated to 50° C., the pressure was reduced gradually to 4.0 kPa over two hours, and the reaction was continued while by-product water was removed. Furthermore, excessive ethyl cyanoacetate was distilled under 130 Pa at 110° C. Then, 921 g of the concentrated liquid thus obtained was subjected to gas chromatography quantitative analysis. As a result, the conversion ratio of the 2-cyclohexylpropanal (II) was 100% and the ethyl 2-cyano-4-cyclohexylpenta-2-enoate (VII-1) had a purity of 98.0% and a reaction yield of 95.9%.

Workup

  1. customa reaction yield of 95.9%

Sources & evidence

ORD record
ord-aeb9dae6af8b4d3283d48d3a5f43de0d
Source dataset
uspto-grants-2016_09
Patent number
US09447362B2

Reaction notes

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