Sodium Hydroxide → Perilla alcohol

HRID 2276626Notes

Reaction equation

HRID 2276626 reaction equation
[OH-].[Na+].[C:3]([CH:6]1[CH2:11][CH2:10][C:9]([CH2:12][O:13]C(=O)C2C=C([N+]([O-])=O)C=C([N+]([O-])=O)C=2)=[CH:8][CH2:7]1)([CH3:5])=[CH2:4]>CO>[CH3:5][C:3]([C@@H:6]1[CH2:7][CH:8]=[C:9]([CH2:12][OH:13])[CH2:10][CH2:11]1)=[CH2:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 76808642HCID 76808642, compound

Product 1

HCID 369312Perilla alcoholYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous sodium hydroxide (3.23 g, 80.0 mmol, dissolved in 28 mL of water) was added to an ice cold solution of 3, 5-Dinitro-benzoic acid 4-isopropenyl-cyclohex-1-enylmethyl ester (14.0 g, 40.4 mmol) in methanol (140 mL) over a period of 0.25 h. The reaction mixture was allowed to warm to room temperature and then stirred for 3.0 h. The methanol was concentrated under vacuum and the resulting residue was suspended in water (60 mL) and extracted with ethyl acetate (2×100 mL). The organic layer was washed with water (2×100 mL) followed by brine (15%, 100 mL) and dried over sodium sulphate (30 g). The filtered organic layer was concentrated under vacuum to get pure (S)-perillyl alcohol (Weight: 5.84 g, Yield: 95% Purity: 99.4% by GC).

Workup

  1. concentrationThe methanol was concentrated under vacuum
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe organic layer was washed with water (2×100 mL)
  4. dry with materialdried over sodium sulphate (30 g)
  5. concentrationThe filtered organic layer was concentrated under vacuum

Sources & evidence

ORD record
ord-5febcb18f71f4c69b62841198c55c67e
Source dataset
uspto-grants-2015_09
Patent number
US09133085B2

Reaction notes

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