HCID 74020198, compound → HCID 74020197, compound

To a dry 5 liter multi-neck round bottom flask fitted with an air stirrer, nitrogen inlet condenser and an addition funnel 1.617 g of CH3Li was added and stirred. 336 g of 4-methyl-3-decene-5-one (see example A for preparation of 3-decene-4-methyl-5-one) was added dropwise over 105 minutes. The temperature of the reaction rose to 63° C. The reaction mixture was aged for 150 minutes and a first sample was taken at 37° C. 30 minutes later, a second sample was taken at 30° C. The mixture was quenched with acetic acid, allowed to settle and layers separated. The aqueous layer was washed twice with 100 ml of toluene. The toluene extracts were added to the organic layer and washed with Na2CO3. The NMR spectrum of the 4.5-Dimethyl-3-decene-5-ol is as follows: 0.88 ppm (t, 3H); 0.94 ppm (t, 3H); 1.28 ppm (s, 3H); 1.15-1.35 ppm (m, 6H); 1.50 ppm (s, 1H); 1.55 ppm (s,1H), 2.05 ppm (m, 2H); ; 5.45 ppm (m, 1 H) The IR spectrum of the 4.5-Dimethyl-3-decene-5-ol is as follows: OH-stretch broad at 3416 cm−1, CH-stretch saturated at 2960, 2933, 2872 cm−1, double bond stretch at 1680 cm−1, 1462 and 1372 due to CH stretch.

1. additionwas added
2. customrose to 63° C
3. customwas taken at 37° C
4. custom30 minutes
5. customwas taken at 30° C
6. customThe mixture was quenched with acetic acid
7. customlayers separated
8. washThe aqueous layer was washed twice with 100 ml of toluene
9. additionThe toluene extracts were added to the organic layer
10. washwashed with Na2CO3

ORD record

ord-0ceae287d09341dfaa60e642f7839971

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07491684B2