Hydrochloric Acid → 4,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazoline

HRID 1080901Notes

Reaction equation

HRID 1080901 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][O:20]C3CCCCO3)=[CH:15][CH:14]=2)=[N:3]1.Cl.C(=O)([O-])O.[Na+]>CO>[CH3:1][C:2]1([CH3:27])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:14]=[CH:15][C:16]([CH2:19][OH:20])=[CH:17][CH:18]=2)=[N:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 153808764,4-Dimethyl-2-(4'-tetrahydropyranyloxymethylbiphenyl-2-yl)oxazoline

Product 1

HCID 110658764,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazolineYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.0 g (10.9 mmol) of 4,4-dimethyl-2-(4'-tetrahydropyranyloxymethyl-biphenyl-2-yl)oxazoline was dissolved in methanol (50 ml), and 6N hydrochloric acid (15 ml) was added thereto, followed by stirring at room temperature for 2 hours. The reaction liquid was poured into a saturated aqueous solution of sodium hydrogencarbonate, followed by the extraction with chloroform. After washing with water and drying, vacuum concentration was conducted. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 3.0 g of the title compound (yield 98%).

Workup

  1. customThe reaction liquid
  2. extractionfollowed by the extraction with chloroform
  3. washAfter washing with water
  4. customdrying
  5. concentrationvacuum concentration
  6. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-141ccd28c1e84f00a0a218a6d7b98ab3
Source dataset
uspto-grants-1996_12
Patent number
US05583229

Reaction notes

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