Sodium Hydroxide → HCID 20242259, compound

HRID 1380212Notes

Reaction equation

HRID 1380212 reaction equation
O[C:2]1([C:12]#[C:13][C:14]([CH3:18])=[CH:15][CH2:16][OH:17])[C:7]([CH3:9])([CH3:8])[CH2:6][C:5](=[O:10])[CH:4]=[C:3]1[CH3:11].[OH-].[Na+]>C(O)CC.O.[Zn]>[OH:17][CH2:16][CH2:15][C:14]([CH3:18])=[C:13]=[CH:12][CH:2]1[C:7]([CH3:8])([CH3:9])[CH2:6][C:5](=[O:10])[CH:4]=[C:3]1[CH3:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 543782774-Hydroxy-4-(5-hydroxy-3-methyl-3-penten-1-ynyl)-3,5,5-trimethyl-2-cyclohexen-1-one

Product 1

HCID 20242259HCID 20242259, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 22595341Propanol waterSolvent

Procedure

10 g (40 mmol) of 4-hydroxy-4-(5-hydroxy-3-methyl-3-penten-1-ynyl)-3,5,5-trimethyl-2-cyclohexen-1-one (prepared in accordance with Example 1) were dissolved in 200 ml of n-propanol/water (1:1, v/v) under argon in a 500 ml multi-necked flask provided with stirrer, thermometer, dropping funnel and gasification headpiece and treated with 20.9 g (0.32 g-atoms) of zinc powder. Thereupon, 120 ml (0.12 mol) of 1N sodium hydroxide solution were added dropwise thereto in 5 minutes at room temperature while stirring and the mixture was stirred for a further 1 hour. The resulting mixture was then worked-up in a manner analogous to that described in Example 1 and there were obtained 9.2 g of crude product. The purification on silica gel in a manner analogous to that described in Example 1 gave 6.9 g (74.3%) of 4-(5-hydroxy-3-methyl-1,2-pentadienyl)-3,5,5-trimethyl-2-cyclohexen-1-one in the form of an oil. The structure of this compound was characterized unequivocally by microanalysis, NMR, IR and MS spectra.

Workup

  1. customv/v) under argon in a 500 ml multi-necked flask provided with stirrer
  2. stirringthe mixture was stirred for a further 1 hour
  3. customthere were obtained 9.2 g of crude product
  4. customThe purification on silica gel in a manner analogous to

Sources & evidence

ORD record
ord-1e1b2e75ec8b4e0889625c4cd485d4f7
Source dataset
uspto-grants-1986_04
Patent number
US04579973

Reaction notes

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