Water → HCID 10171447, compound

HRID 1768446Notes

Reaction equation

HRID 1768446 reaction equation
[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[CH:6][C:7]([CH3:16])=[C:8]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:9]=2)[CH2:4][CH2:3]1.O=O.O.C([O:25]C)(C)(C)C>C(O)(=O)C>[CH3:17][C:2]1([CH3:1])[C:10]2[C:5](=[CH:6][C:7]([CH3:16])=[C:8]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:9]=2)[C:4](=[O:25])[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 977OxygenHCID 15413tert-Butyl methyl etherHCID 113337443,3,6-trimethyl-5-butoxy-indane

Product 1

HCID 10171447HCID 10171447, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

100 g 3,3,6-trimethyl-5-butoxy-indane are dissolved in 400 g acetic acid and 1 g Co-II acetate is added. The reaction mixture is heated to 40° C., with stirring, and oxygen is passed through this solution for 10 hours. After cooling to room temperature, 500 g water and 500 g methyl tert.-butyl ether are added. After phase separation, the organic phase is rinsed with a further 200 g water and distilled in a 30 cm packed column. 80 g 3,3,6-trimethyl-5-butoxy-indan-1-one is obtained, which corresponds to a yield of 75% of theory. The compound can be recrystallised from heptane and a white solid is obtained, melting point: 59° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. customAfter phase separation
  3. washthe organic phase is rinsed with a further 200 g water
  4. distillationdistilled in a 30 cm

Sources & evidence

ORD record
ord-e95ca16bb51042ed9e3faaea669f8e17
Source dataset
uspto-grants-2007_06
Patent number
US07235699B2

Reaction notes

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