Formaldehyde → HCID 22914162, compound

HRID 1377443Notes

Reaction equation

HRID 1377443 reaction equation
[CH3:1][C:2]1([CH3:12])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:9][CH:10]=[O:11].[CH2:13]=O>C(NCC)C>[CH3:1][C:2]1([CH3:12])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]2[C:9](=[CH2:13])[CH:10]=[O:11]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 13658455HCID 13658455, compound

Product 1

HCID 22914162HCID 22914162, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8021DiethylamineCatalyst

Procedure

In a similar manner to Example 49, 342 g of 6,6-dimethylbicyclo[3.1.1]hept-2-yl acetaldehyde at a purity of 97% (1.99 moles), 178 g of 37% formaldehyde (2.2 moles), 7.3 g of diethylamine (0.1 mole), and 0.8 g of BHT were refluxed for 1.5 hours. After the usual work-up, 370 g of crude propenal was distilled to afford 317 g of purified product (89% yield). BP 75° C./0.5 mmHg; 1H-NMR (300 MHz), δ 0.92 (3H, s), 1.23 (3H, s), 1.47-2.40 (8H, m), 3.1 (1H, t, J=8.91 Hz), 5.91 (1H, s), 6.20 (1H, s), 9.50 (1H, s); 13C-NMR (75 MHz), δ 20.06, 20.92, 23.88, 26.76, 28.03, 32.82, 40.08, 41.32, 44.34, 131.53, 155.46, 194.97; IR (Neat), 2960, 2700, 1690, 940 cm-1 ; MS (m/e), 177 (M+ -1), 163, 145, 135, 121, 107, 91, 79, 41 (Base);

Workup

  1. distillationAfter the usual work-up, 370 g of crude propenal was distilled

Sources & evidence

ORD record
ord-2b1d18d212bb4251a62c3c41122cf943
Source dataset
uspto-grants-1997_09
Patent number
US05665696

Reaction notes

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