3-Chloro-2-methyl-1-propene → HCID 22914112, compound

HRID 1377450Notes

Reaction equation

HRID 1377450 reaction equation
[CH3:1][C:2]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH:11]=[O:12])[CH2:6]1)([CH3:4])[CH3:3].[CH3:13][C:14]([CH3:17])([O-])[CH3:15].[K+].C(Cl)C(=C)C>CN(C=O)C>[CH3:15][C:14](=[CH2:13])[CH2:17][C:7]1([CH:11]=[O:12])[CH2:8][CH2:9][CH2:10][CH:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:6]1

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 12931805HCID 12931805, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22914112HCID 22914112, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
155 °C

Procedure

Similar to Example 6, 17.0 g of 3-(1,1-dimethylethyl)cyclohexane carboxaldehyde (prepared by the method of E. Heilweil and J. Virgilio, Organic Preparations and Procedures, 14 (1-2), 9 (1982) at a purity of 87% (0.088 mole) in 20 ml of DMF, 11.9 g of potassium t-butoxide (0.10 mole) in 60 ml of DMF, and 12.0 g of methallyl chloride (0.13 mole) in 10 ml of DMF were reacted in the usual manner. The resulting mixture of O- and C-alkylates, 21.6 g, was heated at 155° C. for 1 hour. The crude aldehyde so obtained, 19 g, was distilled to afford 8.7 g of purified product (45% yield). BP 57° C./0.1 mmHg; 1H-NMR (300 MHz), δ 0.85 (9H, s), 0.97-1.45 (3H, m), 1.66 (3H, s), 1.68-1.74 (3H, m), 2.03-2.40 (5H, m), 4.66 (1H, s), 4.84 (1H, s), 9.50 (1H, s); 13C-NMR (75 MHz), δ 23.26, 24.63, 26.60, 27.34, 31.40, 32.46, 33.79, 44.31, 47.74, 50.56, 115.33, 140.77, 207.33; IR (Neat), 2970, 2690, 1720, 1635, 1450, 1360, 895 cm-1 ; MS (m/e), 222 (M+), 207, 166 (Base), 137, 123, 109, 95, 81, 57, 41.

Workup

  1. additionThe resulting mixture of O- and C-alkylates, 21.6 g
  2. customThe crude aldehyde so obtained
  3. distillation19 g, was distilled

Sources & evidence

ORD record
ord-2b50767cc98640c3895a9680f7f3b87a
Source dataset
uspto-grants-1997_09
Patent number
US05665696

Reaction notes

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