Pinacolone → 1-[4-(1,3-Dioxolan-2-yl)phenyl]-4,4-dimethylpent-1-en-3-one

HRID 652581Notes

Reaction equation

HRID 652581 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[CH3:14][C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16]>C(O)C.O.[OH-].[Na+]>[CH3:18][C:17]([CH3:20])([CH3:19])[C:15](=[O:16])[CH:14]=[CH:10][C:9]1[CH:12]=[CH:13][C:6]([CH:2]2[O:3][CH2:4][CH2:5][O:1]2)=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 6416PinacoloneHCID 118299884-(1,3-Dioxolan-2-yl)benzaldehyde

Product 1

HCID 543458391-[4-(1,3-Dioxolan-2-yl)phenyl]-4,4-dimethylpent-1-en-3-oneYield 39%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

100 g (0.5612 mol) of 4-(1,3-dioxolan-2-yl)-benzaldehyde and 56.1 g (0.56 mol) of pinacoline are dissolved in a mixture of 280 ml of ethanol and 56 ml of water, and 17 ml of 10% strength sodium hydroxide solution are added at room temperature. The mixture is subsequently stirred for 1 hour, 0.56 g of solid sodium hydroxide are added and the mixture is subsequently stirred for 2 days. Thereafter, the precipitate is filtered off with suction, washed with 200 ml of ethanol/water (1:1) and then with water, dried and recrystallized twice from ethanol. 56.5 g (39% of theory) of 4,4-dimethyl-1-[4-(1,3-dioxolan-2-yl)-phenyl]-1-penten-3-one of melting point 79°-81° C. are obtained.

Workup

  1. additionare added at room temperature
  2. stirringthe mixture is subsequently stirred for 2 days
  3. filtrationThereafter, the precipitate is filtered off with suction
  4. washwashed with 200 ml of ethanol/water (1:1)
  5. dry with materialwith water, dried
  6. customrecrystallized twice from ethanol

Sources & evidence

ORD record
ord-dfd0033225d543a6a6ec28012d2cbc4b
Source dataset
uspto-grants-1987_06
Patent number
US04672134

Reaction notes

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