Potassium Hydroxide → 119454-82-9

HRID 2076431Notes

Reaction equation

HRID 2076431 reaction equation
[CH3:1][C:2]1([CH3:26])[C:11]2[C:6](=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[C:5]([CH3:25])([CH3:24])[CH2:4][CH2:3]1.[OH-].[K+]>O>[CH3:1][C:2]1([CH3:26])[C:11]2[C:6](=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:22][CH:23]=3)=[CH:9][CH:10]=2)[C:5]([CH3:25])([CH3:24])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13655815HCID 13655815, compound

Product 1

HCID 6439770119454-82-9Yield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

In a 50 mL round bottom flask was charged methyl 4-((E)-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)vinyl)benzoate 10 (0.30 g, 0.86 mmol) in 20 mL and water (2 mL) and KOH was added (193 mg, 3.44 mmol). The suspension was heated for 6 h at 70° C. Methanol was removed in vacuo, water (20 mL) was added and the solution washed with diethyl ether (2×30 mL). The aqueous solution was carefully acidified to pH=1 using a solution of HCl 1N and extracted with diethyl ether (3×100 ml). The organic layer was dried over MgSO4, filtered and evaporated to yield to 4-((E)-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)vinyl)benzoic acid 12 (0.26 g, 90% yield) as a white solid.

Workup

  1. additionwas added (193 mg, 3.44 mmol)
  2. customMethanol was removed in vacuo, water (20 mL)
  3. additionwas added
  4. washthe solution washed with diethyl ether (2×30 mL)
  5. extractionextracted with diethyl ether (3×100 ml)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a9a8d9329bc64806a2f28ad901b64232
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

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