Cyclohexene → HCID 15383566, compound

HRID 1600488Notes

Reaction equation

HRID 1600488 reaction equation
[OH:1][C:2]1[C:17]([CH2:18][CH:19]([CH3:33])[CH2:20][Si:21]([CH3:32])([O:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[O:22][Si:23]([CH3:26])([CH3:25])[CH3:24])=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([O:6]CC1C=CC=CC=1)=[O:5].C1CCCCC=1>[Pd].C(O)C>[OH:1][C:2]1[C:17]([CH2:18][CH:19]([CH3:33])[CH2:20][Si:21]([CH3:32])([O:27][Si:28]([CH3:29])([CH3:31])[CH3:30])[O:22][Si:23]([CH3:26])([CH3:25])[CH3:24])=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 15383567HCID 15383567, compound

Product 1

HCID 15383566HCID 15383566, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the above crude oil of benzyl 2-hydroxy-3-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propyl]benzoate (11.61 g, 0.023 mol), ethanol (40 ml), cyclohexene (12 ml) and 10% palladium-on-charcoal (1.2 g) was maintained at reflux for 1 hour. The mixture was cooled and rinsed with ethanol. The liquids were concentrated and the pale yellow oil obtained was purified by chromatography on silica under pressure (eluent: 80/20/0.2 CH2Cl2 /ethyl acetate/acetic acid) to give 7.5 g (yield: 78%) of 2-hydroxy-3-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]-propyl]benzoic acid in the form of a colourless oil.

Workup

  1. temperaturewas maintained
  2. temperatureat reflux for 1 hour
  3. temperatureThe mixture was cooled
  4. washrinsed with ethanol
  5. concentrationThe liquids were concentrated
  6. customthe pale yellow oil obtained
  7. customwas purified by chromatography on silica under pressure (eluent: 80/20/0.2 CH2Cl2 /ethyl acetate/acetic acid)

Sources & evidence

ORD record
ord-5ad80a9a277945fcab40f16bdad80cce
Source dataset
uspto-grants-1999_11
Patent number
US05976558

Reaction notes

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