HCID 4577356, compound → 2-Hydroxycyclopentadecan-1-one
Reaction equation
OC1CCCCCCCCCCCC1=O.C([O:19][CH:20]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][C:21]1=[O:35])(=O)C.C(OC1CCCCCCCCCCCC1=O)(=O)C.OC1CCCCCCCCCCCCCCC1=O>>[OH:35][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:20]1=[O:19]Participants
Procedure
Thirty grams each of 2-hydroxycyclopentadecanone, 2-hydroxycyclotridecanone, 2-acetoxycyclopentadecanone, 2-acetoxycyclotridecanone, and 2-hydroxycyclohexadecanone obtained through acyloin condensation was dissolved in 200 ml of an organic solvent shown in Table 1. The resulting solution was placed in a reaction apparatus equipped with a reflux condener having a water trap, a stirrer, and a dropping funnel, and 40 g of a zinc powder was dispersed therein. The mixture was allowed to react under reflux by adding 150 ml of 12N hydrochloric acid dropwise over a period of 1.5 hours. During the reaction, the aqueous layer in the trap was intermittently withdrawn in the case of using toluene, xylene, or cyclohexane as an organic solvent. In the case of using methyl ethyl ketone, the whole amount of the liquid reserved in the trap (about 90 ml) was intermittently withdrawn.
Sources & evidence
- ORD record
- ord-2fa0293147e846818e8c0069ae9cbc78
- Source dataset
- uspto-grants-1987_10
- Patent number
- US04700007
Reaction notes
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