Ethanol → (Z)-4-[2-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-(trimethylsilyl)vinyl]benzoic Acid

HRID 1281227Notes

Reaction equation

HRID 1281227 reaction equation
[CH3:1][C:2]1[C:3](/[C:16](/[Si:29]([CH3:32])([CH3:31])[CH3:30])=[CH:17]/[C:18]2[CH:28]=[CH:27][C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][CH:19]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.C(O)C.[OH-].[K+]>O>[CH3:1][C:2]1[C:3](/[C:16](/[Si:29]([CH3:30])([CH3:32])[CH3:31])=[CH:17]/[C:18]2[CH:28]=[CH:27][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 9955320Ethyl(Z)-4-[2-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-(trimethylsilyl)vinyl]benzoate2×

Product 1

HCID 9910061(Z)-4-[2-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-(trimethylsilyl)vinyl]benzoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl (Z)-4-[2-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-(trimethylsilyl)vinyl]benzoate (Compound 4, 0.034 g, 0.076 mmol) and 2 mL of ethyl alcohol was added aqueous 1 N KOH (0.5 mL). The resulting solution was heated in an 50° C. bath until the hydrolysis reaction was completed, as judged by thin layer chromatography. The solution was cooled to room temperature, diluted with water and washed once with 1:1 ether:hexane solution, and the layers were separated. The aqueous layer was acidified with 1 N aqueous HCl and the product extracted 3 times with ethyl acetate. The combined organic extracts were washed with brine, and dried over MgSO4, and filtered, and the solvents were removed in vacuo to give the title compound as a white solid.

Workup

  1. customuntil the hydrolysis reaction
  2. temperatureThe solution was cooled to room temperature
  3. washwashed once with 1:1 ether
  4. customhexane solution, and the layers were separated
  5. extractionthe product extracted 3 times with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-ea6d8f96f8bb45d39f7381ce349bca33
Source dataset
uspto-grants-2002_09
Patent number
US06452032B1

Reaction notes

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