Allyl chloride → HCID 22914138, compound

HRID 1721276Notes

Reaction equation

HRID 1721276 reaction equation
[CH3:1][CH:2]([CH:5]([CH3:11])[CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:3]=[O:4].[CH3:12][C:13](C)([O-])[CH3:14].[K+].C(Cl)C=C>CN(C=O)C>[CH3:1][C:2]([CH:5]([CH2:6][C:7]([CH3:9])([CH3:8])[CH3:10])[CH3:11])([CH2:14][CH:13]=[CH2:12])[CH:3]=[O:4]

Participants

5

Reactant 3

HCID 7850Allyl chlorideHCID 109323Hexanal, 2,3,5,5-tetramethyl-HCID 23665647Potassium tert-butoxide

Product 1

HCID 22914138HCID 22914138, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

In a similar manner to Example 6, 100 g of the aldehyde from Example 72 at a purity of 96% (0.61 mole) in 50 ml of DMF, 80 g of potassium t-butoxide (0.68 mole) in 500 ml of DMF, and 53 g of allyl chloride (0.69 mole) in 50 ml of DMF were reacted in the usual manner. In this way 90.5 g of crude O- and C-alkylates (65.7:9.6) and 12.2% of starting material were produced. The crude product was heated at 155°-170° C. for 3 hours to afford 87 g of crude aldehyde. This material was distilled to afford 51 g of purified product (43% yield). BP 45° C./0.15 mmHg; 1H-NMR (300 MHz), δ0.89 (9H, s), 0.93 (3H, s), 0.94 (1H, m), 0.98 (3H, d, J=6.84 Hz), 1.2 (1H, m), 1.84 (1H, m), 2.18 (1H, m), 2.35 (1H, m), 5.06 (2H, m), 5.67 (1H, m), 9.45 (1H, s); 13C-NMR (75 MHz), δ13.99, 16.69, 18.15, 30.03, 32.54, 38.98, 46.38, 53.29, 118.23, 133.47, 207.26; IR (Neat), 2960, 2700, 1730, 1640, 1480, 1370, 920 cm-1 ; MS (m/e), 181 (M+ -15), 98, 83, 69, 57 (Base);

Sources & evidence

ORD record
ord-9d0ba48ea2a34eaaa5094925bf320bd3
Source dataset
uspto-grants-1996_04
Patent number
US05510326

Reaction notes

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