Water → HCID 67660500, compound

HRID 1599138Notes

Reaction equation

HRID 1599138 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][C:7](=[O:9])[CH:6]=[CH:5][CH2:4]1.[C:10](Cl)(=[O:12])[CH3:11].O>ClCCl>[C:10]([O:1][CH2:2][C@H:3]1[CH2:8][C:7](=[O:9])[CH:6]=[CH:5][CH2:4]1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 10374469HCID 10374469, compound

Product 1

HCID 67660500HCID 67660500, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

76 cm3 of triethylmmine are added to a solution, cooled to +5° C., of 62 g of (R)-5-hydroxymethylcyclohex-2-en-1-one [prepared according to the method described by Kenji Mori et al., Tetrahedron, Vol. 48, No. 24, 8075-8082 (1990) incorporated herein by reference] in 600 cm3 of dry dichloromethane, and then 38.4 cm3 of acetyl chloride are run in over the course of 30 minutes. After stirring at +5° C. for one hour and at 20° C. for one hour, 1 liter of water is added slowly to the mixture. The separated organic phase is washed with 1 liter of water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). 80 g of (R)-5-acetoxymetylcyclohex-2-en-1-one are obtained in the form of an orange-coloured oil.

Workup

  1. addition76 cm3 of triethylmmine are added to a solution
  2. customprepared
  3. customare run in over the course of 30 minutes
  4. washThe separated organic phase is washed with 1 liter of water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-b9b0de9b8c084f9ca74915642364745d
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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