3-Chloro-2-methyl-1-propene → HCID 22914091, compound

HRID 1377446Notes

Reaction equation

HRID 1377446 reaction equation
[CH3:1][C:2]1([CH3:13])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]2[CH:9]([CH3:12])[CH:10]=[O:11].[CH3:14][C:15]([CH3:18])([O-])[CH3:16].[K+].C(Cl)C(=C)C>CN(C=O)C>[CH3:12][C:9]([CH:6]1[CH2:5][CH2:4][CH:3]2[CH2:8][CH:7]1[C:2]2([CH3:13])[CH3:1])([CH2:16][C:15]([CH3:18])=[CH2:14])[CH:10]=[O:11]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 22914156HCID 22914156, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22914091HCID 22914091, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

In a similar manner to Example 6, 100 g of the aldehyde from Example 58 at a purity of 85% (0.47 mole) in 75 ml of DMF, 82 g of potassium t-butoxide (0.69 mole) in 500 ml of DMF, and 78 g of methallyl chloride (0.86 mole) in 50 ml of DMF were reacted in the usual way. In this way 116.2 g of crude O- and C-alkylates (58.1:33.8) were obtained. The crude product was heated at 165°-170° C. for 2 hours. The crude aldehyde was distilled to afford 94.1 g of purified product (85% yield). BP 85° C./0.05 mmHg; 1H-NMR (300 MHz), δ 0.95 (3H, s), 0.96 (3H, s), 1.18 (3H, s), 1.2-1.4 (2H, m), 1.59 (3H, s), 1.7-2.5 (9H, m), 4.64 (1H, s), 4.80 (1H, s), 9.57 (1H, s); 13C-NMR (75 MHz), spectra consistent with assigned structures; IR (Neat), 2960, 2700, 1725, 1645, 1470, 1370, 895 cm-1 ; MS (m/e), 234 (M+), 219, 203, 191, 177, 163, 151, 135, 123, 109, 97, 81, 41 (Base);

Workup

  1. customIn this way 116.2 g of crude O- and C-alkylates (58.1:33.8) were obtained
  2. distillationThe crude aldehyde was distilled

Sources & evidence

ORD record
ord-0d6156ab524b496c93a00bab10eeb693
Source dataset
uspto-grants-1997_09
Patent number
US05665696

Reaction notes

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