Gamma-Butyrolactone → 1,3-Dioxo-6-hydroxy-1(3'-tert-butyl-phenyl)-hexane

HRID 733178

Reaction equation

HRID 733178 reaction equation
[H-].[Na+].[C:3]1(=[O:8])[O:7][CH2:6][CH2:5][CH2:4]1.[C:9]([C:13]1[CH:14]=[C:15]([C:19](=[O:21])[CH3:20])[CH:16]=[CH:17][CH:18]=1)([CH3:12])([CH3:11])[CH3:10].[Cl-].[NH4+]>CCOCC.C(O)C>[O:21]=[C:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:14]=1)[CH2:20][C:3](=[O:8])[CH2:4][CH2:5][CH2:6][OH:7]

Participants

7

Reactant 4

HCID 7302Gamma-ButyrolactoneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 136579781-(3-tert-Butylphenyl)ethan-1-one

Product 1

HCID 578391201,3-Dioxo-6-hydroxy-1(3'-tert-butyl-phenyl)-hexane

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirring suspension of NaH (60% in oil, 7.66 g) in ether (480 ml) at 0° C. was added ethanol (479 μL), followed by γ-butyrolactone (6.18 ml). This was followed by dropwise addition of 1-(3-tert-butyl-phenyl)-ethanone (13.5 g) in ether (80 ml). The resulting mixture was allowed to warm to room temperature and stirred for 72 hours. After careful addition of ethanol (10.5 ml), ammonium chloride solution (10 g in 250 ml water) was then added, ether layer was then separated and washed with brine (300 ml), dried over MgSO4 and concentrated in vacuo to give 1,3-dioxo-6-hydroxy-1(3′-tert-butyl-phenyl)-hexane as crude product (18.5 g). This required no purification and was immediately used in the next reaction.

Workup

  1. additionwas then added
  2. customether layer was then separated
  3. washwashed with brine (300 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44a0741dc5894e7abf0078fe50f4a301
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Linked notes

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