Hydrochloric Acid → HCID 86655402, compound

HRID 2190472Notes

Reaction equation

HRID 2190472 reaction equation
[CH3:1][C:2]([O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12]C)=[O:11])([CH3:5])[C:3]#[CH:4].CO.O.Cl>O1CCCC1>[CH3:5][C:2]([O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([OH:12])=[O:11])([CH3:1])[C:3]#[CH:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 76333229Methyl 3-[(1,1-dimethylprop-2-yn-1-yl)oxy]benzoate

Product 1

HCID 86655402HCID 86655402, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[(1,1-dimethylprop-2-yn-1-yl)oxy]benzoate (4.0 g, 18.3 mmol) in tetrahydrofuran (10 mL) were added lithium hydroxide•monohydrate (865 mg, 20.6 mmol), methanol (10 mL) and water (5 mL), and the mixture was stirred at room temperature for 12 hr. The reaction mixture was adjusted to pH 3 by slowly adding 1N hydrochloric acid, and extracted with ethyl acetate (100 mL×2). The ethyl acetate layers were combined, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (3.8 g, 99%) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate (100 mL×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2a1f052b16c740dd91986ce7ca1879c8
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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