Acetic Anhydride → HCID 14631299, compound

HRID 483897Notes

Reaction equation

HRID 483897 reaction equation
[OH:1][C@@H:2]1[CH2:7][C@@H:6]([CH3:8])[C:5](=[O:9])[C:4]([CH3:11])([CH3:10])[CH2:3]1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>N1C=CC=CC=1>[C:12]([O:1][C@@H:2]1[CH2:7][C@@H:6]([CH3:8])[C:5](=[O:9])[C:4]([CH3:10])([CH3:11])[CH2:3]1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10313234Cyclohexanone, 4-hydroxy-2,2,6-trimethyl-, (4R,6R)-

Product 1

HCID 14631299HCID 14631299, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

300 g of (4R, 6R)-4-hydroxy-2,2,6-trimethylcyclohexanone were dissolved in 154.7 ml of pyridine. The solution was treated dropwise at -3° C. to 0° C. within 10 minutes with 1.2 l of acetic anhydride and then stirred at room temperature for a further 4.25 hours. The reaction mixture was subsequently concentrated on a rotary evaporator at 60° C./16 mbar, whereby there were obtained 394.7 g of crude product as a yellow oil. Distillation of the crude product gave at about 95° C./0.07 mbar 378.4 g (99.4%) of (4R, 6R)-4-acetoxy-2,2,6-trimethylcyclohexanone as a colourless oil.

Workup

  1. concentrationThe reaction mixture was subsequently concentrated on a rotary evaporator at 60° C./16 mbar
  2. customwhereby there were obtained 394.7 g of crude product as a yellow oil
  3. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-5e21179d959342439294bf0e246e2ba0
Source dataset
uspto-grants-1993_07
Patent number
US05227507

Reaction notes

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