Vinyl Acetate → (1R,3S)-Cyclohexane-1,3-diyl diacetate

HRID 1717441Notes

Reaction equation

HRID 1717441 reaction equation
[C@H:1]1([OH:8])[CH2:6][CH2:5][CH2:4][C@H:3]([OH:7])[CH2:2]1.[C:9](OC=C)(=[O:11])[CH3:10].[C:15]([O:19]C)(C)(C)[CH3:16]>>[C:9]([O:7][C@H:3]1[CH2:4][CH2:5][CH2:6][C@@H:1]([O:8][C:15](=[O:19])[CH3:16])[CH2:2]1)(=[O:11])[CH3:10]

Participants

4

Reactant 3

HCID 7904Vinyl AcetateHCID 15413tert-Butyl methyl etherHCID 6432541HCID 6432541, compound

Product 1

HCID 14172810(1R,3S)-Cyclohexane-1,3-diyl diacetateYield 23%

Procedure

30 g of a 60 to 40 mixture of cis/trans-cyclohexane-1,3-diol are dissolved in 900 ml of methyl tert-butyl ether, 100 ml of vinyl acetate are added and 1.7 g of lipase (Chirazyme L1 lyo.) are added (20° C.). After 24 h, the protein is filtered off and the solvent is removed. The remaining oil is taken up in 1000 ml of cyclohexane and washed four times with 150 ml of water. The organic phase is removed on a rotary evaporator. 10 g of cis-1,3-diacetoxycyclohexane are obtained as an oil (23% yield based on the cis/trans mixture, 95% cis).

Workup

  1. addition1.7 g of lipase (Chirazyme L1 lyo.) are added (20° C.)
  2. filtrationthe protein is filtered off
  3. customthe solvent is removed
  4. washwashed four times with 150 ml of water
  5. customThe organic phase is removed on a rotary evaporator

Sources & evidence

ORD record
ord-48112e91fc7d40e58398cfa27c18b32b
Source dataset
uspto-grants-2010_09
Patent number
US07803950B2

Reaction notes

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