Potassium Hydroxide → HCID 10088269, compound

HRID 2076432Notes

Reaction equation

HRID 2076432 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 58893574HCID 58893574, compound

Product 1

HCID 10088269HCID 10088269, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

In a 50 mL round bottom flask was charged methyl 4-((Z)-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)vinyl)benzoate 11 (0.16 g, 0.46 mmol) in 15 mL and water (1.5 mL) and KOH was added (103 mg, 1.84 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 (2×50 mL). The aqueous solution was carefully acidified to pH=1 using a solution of HCl 1N and extracted with diethyl ether (3×50 ml). The organic layer was dried over MgSO4, filtered and evaporated to yield to 4-((Z)-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)vinyl)benzoic acid 13 (0.151 g, 98% yield) as a white solid.

Workup

  1. additionwas added (103 mg, 1.84 mmol)
  2. customMethanol was removed in vacuo, water (20 mL)
  3. additionwas added
  4. washthe solution washed with diethyl ether (2×50 mL)
  5. extractionextracted with diethyl ether (3×50 ml)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-46d8c78c96834c8895157ba82b34c46e
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

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