Water → 1-[4-(1-Hydroxyethyl)-phenyl]-3,3-dimethylbutan-1-one

HRID 2041565Notes

Reaction equation

HRID 2041565 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][C:4]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1)=[O:5].[CH3:16][Mg]Br.O>C1COCC1.CCOC(C)=O>[OH:11][CH:10]([C:9]1[CH:8]=[CH:7][C:6]([C:4](=[O:5])[CH2:3][C:2]([CH3:15])([CH3:14])[CH3:1])=[CH:13][CH:12]=1)[CH3:16]

Participants

6

Reactant 3

HCID 962WaterHCID 576561564-(3,3-Dimethyl-butyryl)-benzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 576565131-[4-(1-Hydroxyethyl)-phenyl]-3,3-dimethylbutan-1-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

Dissolve 4-(3,3-dimethyl-butyryl)-benzaldehyde (1.67 g, 8.186 mmol) in anhydrous THF (20 mL) and cool the solution at −10° C. Add methyl magnesium bromide (2.7 mL, 8.186 mmol, 3M solution in diethyl ether) and stir the mixture for 30 min. Add water at 0° C., dilute with EtOAc and extract the aqueous layer three times with EtOAc. Dry the combined organic extracts over Na2SO4, filter through a short pad of silica gel and concentrate in vacuo to .give the desired intermediate as yellow oil (1.519 g, 84%).

Workup

  1. extractionextract the aqueous layer three times with EtOAc
  2. dry with materialDry the combined organic extracts over Na2SO4
  3. filtrationfilter through a short pad of silica gel
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-5ac93e2e61f34e32b3217c3650dd792b
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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