Hydrochloric Acid → 3,5-Diisopropoxybenzoic acid-1G

HRID 2407598Notes

Reaction equation

HRID 2407598 reaction equation
C(OC1C=CC=CC=1C([O-])=O)(C)C.[CH:14]([O:17][C:18]1[CH:19]=[C:20]([CH:27]=[C:28]([O:30][CH:31]([CH3:33])[CH3:32])[CH:29]=1)[C:21]([O:23]C(C)C)=[O:22])([CH3:16])[CH3:15].[OH-].[Li+].Cl>C1COCC1.O>[CH:31]([O:30][C:28]1[CH:27]=[C:20]([CH:19]=[C:18]([O:17][CH:14]([CH3:16])[CH3:15])[CH:29]=1)[C:21]([OH:23])=[O:22])([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 40493909IsopropoxybenzoateHCID 58261000Isopropyl 3,5-diisopropoxybenzoate

Product 1

HCID 205341403,5-Diisopropoxybenzoic acid-1GYield 55%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Crude isopropoxybenzoate from above (compound E) was dissolved in 200 mL THF/H2O (1:1) in a 500 mL flask. Excess lithium hydroxide (10 g) was added and the reaction refluxed for over 48 hours. The mixture was cooled, acidified with HCl to pH 2, then extracted with several portions of diethyl ether. The organic layers were washed with brine, dried over MgSO4, and concentrated to a white solid in 55% yield over 2 steps: IR (cm−1): 3064, 2978, 2933, 2639, 1693, 1594, 1300, 1158, 1114, 1040, 767; 1H NMR (250 MHz, CD3OD): δ 1.30 (dd, J=2.3, 5.9 Hz, 12H), 4.59 (qn, J=6.2 Hz, 2H), 6.61 (t, J=2.3 Hz, 1H), 7.10 (d, J=2.5 Hz, 2H); 13C NMR (63 MHz, CD3OD): 22.2 (4C), 71.2 (2C), 109.8, 109.9, 133.8, 160.3 (2C), 169.7.

Workup

  1. temperaturethe reaction refluxed for over 48 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with several portions of diethyl ether
  4. washThe organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to a white solid in 55% yield over 2 steps

Sources & evidence

ORD record
ord-78b973d28d084764b42b098d160eea7a
Source dataset
uspto-grants-2014_08
Patent number
US08809563B2

Reaction notes

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