Hydrochloric Acid → 4-Hydroxy-3-(3-methylbut-2-en-1-yl)benzoic acid

HRID 2272762Notes

Reaction equation

HRID 2272762 reaction equation
[OH-].[Li+].C([O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][C:8]=1[CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])(=O)C.C1COCC1.CO.O.Cl>C1COCC1>[OH:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21892291Methanol tetrahydrofuran waterHCID 57940298Methyl 4-acetoxy-3-(3-methylbut-2-enyl)benzoate

Product 1

HCID 4438524-Hydroxy-3-(3-methylbut-2-en-1-yl)benzoic acidYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (85 mg, 2.02 mmol) was added to a mixture of methyl ester 7 (106 mg, 0.405 mmol) in 0.5 mL of a 3/1/1 THF/MeOH/H2O solution. The reaction mixture was stirred at reflux for 14 hours, cooled to room temperature, and diluted with THF (1 mL). The solution was acidified the solution to pH=3 by the dropwise addition of 6 M HCl. The layers were separated and the organic phase was dried (Na2SO4), filtered, and concentrated to afford acid 8 (63 mg, 75%) as a red oil that was suitable for use without further purification.

Workup

  1. temperatureat reflux for 14 hours
  2. customThe layers were separated
  3. dry with materialthe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f5c58bbfd2a849a4bd39f7a8d3646e33
Source dataset
uspto-grants-2015_09
Patent number
US09120774B2

Reaction notes

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