Hydrochloric Acid → HCID 130326, compound

HRID 1453623Notes

Reaction equation

HRID 1453623 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][CH:4]=1)=O.[CH3:13][C:14]1([CH3:29])[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[C:20]2[CH:19]=[C:18]([C:26](=[O:28])[CH3:27])[CH:17]=[CH:16][C:15]1=2.Cl>[OH-].[Na+].CO>[O:28]=[C:26]([C:18]1[CH:17]=[CH:16][C:15]2[C:14]([CH3:29])([CH3:13])[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[C:20]=2[CH:19]=1)[CH:27]=[CH:1][C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 15294Methyl 4-FormylbenzoateHCID 27475621-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one2×

Product 1

HCID 130326HCID 130326, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 4-formylbenzoate (1.28 g, 7.83 mmol) was added to a solution of 1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Compound 1, 1.80 g, 7.83 mmol) in 10 mL of 1 N NaOH and 20 mL of methanol. After stirring at room temperature for 18 h, the reaction mixture was acidified with 1N HCl and extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. Recrystallization (acetonitrile) gave the title compound (1.70 g, 60% yield) as a white solid:

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe combined organic layer was washed with brine (1×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated at reduced pressure
  5. customRecrystallization (acetonitrile)

Sources & evidence

ORD record
ord-6910cad55e614936a70bb42cd79bd480
Source dataset
uspto-grants-2009_01
Patent number
US07476673B2

Reaction notes

Loading…