Sodium Hydroxide → 1,3,3-Trichloro-2-methyl-7-oxabicyclo[4.1.0]heptane

HRID 21830

Reaction equation

HRID 21830 reaction equation
ClC12[O:8]C1CCC(Cl)(F)C2.[CH3:11][C:12]1(O)[C:17]([Cl:19])([Cl:18])[CH2:16][CH2:15][CH2:14][C:13]1([Cl:21])Cl.[OH-].[Na+]>O>[Cl:21][C:13]12[O:8][CH:14]1[CH2:15][CH2:16][C:17]([Cl:19])([Cl:18])[CH:12]2[CH3:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 189709521-Methyl-2,2,6,6-tetrachlorocyclohexanolHCID 189709661,3-Dichloro-3-fluoro-7-oxabicyclo[4.1.0]heptane

Product 1

HCID 189709711,3,3-Trichloro-2-methyl-7-oxabicyclo[4.1.0]heptaneYield 95.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The same procedure was employed as for the preparation of 2e in Example 17: it was performed with 3.97 g (15.75 mmol) of crude alcohol 1j, 20 cm3 of distilled water and 2.4 g (60 mmol) of sodium hydroxide; reaction time was 1 h 15 min; ether extraction (5×40 cm3); 3.29 g of epoxide 2h were obtained having a 95.5% yield based on the ketone (macrobore GC purity>99%)

Workup

  1. customreaction time
  2. extractionether extraction (5×40 cm3)

Sources & evidence

ORD record
ord-dba446c7a9b44a30bf42149a03215cf5
Source dataset
uspto-grants-1995_06
Patent number
US05424460

Linked notes

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