Sodium Hydroxide → 6(R),10-dimethyl-undecan-2-yn-4(R)-ol

HRID 26993Notes

Reaction equation

HRID 26993 reaction equation
[N+](C1C=C(C=C([N+]([O-])=O)C=1)C([O:9][C@H:10]([CH2:14][C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:11]#[C:12][CH3:13])=O)([O-])=O.[OH-].[Na+]>CO>[CH3:22][C@H:15]([CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:14][C@@H:10]([OH:9])[C:11]#[C:12][CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 227991316(R),10-Dimethyl-Undecan-2-yn-4(R)-ol 3,5-Dinitrobenzoate

Product 1

HCID 227991326(R),10-dimethyl-undecan-2-yn-4(R)-olYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.65 g (0.0171 mol) of 6(R),10-dimethyl-undecan-2-yn-4(R)-ol 3,5-dinitrobenzoate and 35 ml of 6 N aqueous NaOH in methanol (300 ml) were refluxed for 11/2 hr. It was worked up as in Example 45 to give 3.30 g (98.8%) of pure 6(R),10-dimethyl-undecan-2-yn-4(R)-ol as a colorless oil.

Sources & evidence

ORD record
ord-1b94e2ca83704bf18a638326993a2758
Source dataset
uspto-grants-1979_04
Patent number
US04151360

Reaction notes

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