Cyclohexene → HCID 15383565, compound

HRID 1292023Notes

Reaction equation

HRID 1292023 reaction equation
[OH:1][C:2]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]([CH3:34])[CH2:21][Si:22]([CH3:33])([O:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[O:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[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[CH:17]=[C:16]([O:18][CH2:19][CH:20]([CH3:34])[CH2:21][Si:22]([CH3:33])([O:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[O:23][Si:24]([CH3:26])([CH3:25])[CH3:27])[CH:15]=[CH:14][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 15383564HCID 15383564, compound

Product 1

HCID 15383565HCID 15383565, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 12 g of benzyl 2-hydroxy-4-(2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)-oxy]disiloxanyl]propyloxy]benzoate (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 was rinsed with ethanol. The fluids were concentrated and the resulting product was recrystallized from a 50/50 water/ethanol mixture to give the 2-hydroxy-4-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propyloxy]benzoic acid in the form of a white powder.

Workup

  1. temperaturewas maintained
  2. temperatureat reflux for 1 hour
  3. temperatureThe mixture was cooled
  4. washwas rinsed with ethanol
  5. concentrationThe fluids were concentrated
  6. customthe resulting product was recrystallized from a 50/50 water/ethanol mixture

Sources & evidence

ORD record
ord-7a7f1c0e1891434a8ab7543804710bb6
Source dataset
uspto-grants-1998_05
Patent number
US05756485

Reaction notes

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