Lithium Hydroxide → HCID 19900662, compound

HRID 1029539Notes

Reaction equation

HRID 1029539 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([C:16](=[O:21])[C:17]([O:19]C)=[O:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[Li+].[OH-]>O.CO.O1CCCC1>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([C:16](=[O:21])[C:17]([OH:19])=[O:18])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86745643HCID 86745643, compound

Product 1

HCID 19900662HCID 19900662, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

3,5-Bis(1,1-dimethylethyl)-4-hydroxy-α-oxo-benzeneacetic acid, methyl ester (20.0 g, 68.4 mmol) and LiOH (3.2 g, 439.1 mmol) are combined in 125 mL of a water-methanol-tetrahydrofuran mixture (1:1:1). The reaction warms to ca 50° C. and is maintained at this temperature using a heating bath for 5 hours under nitrogen atmosphere. The reaction is poured onto ice water and extracted with diethyl ether (3×). The cold aqueous layer is acidified with aqueous 12N HCl and extracted with diethyl ether (3×). The combined ethereal layers from the second extraction are washed with saturated aqueous NaCl, dried over Na2SO4, and concentrated in vacuo to give an oil. Crystallizing from diethyl ether/pentane gives 14.0 g of a first crop (mp 125°-126° C.) and 2.7 g as a second crop (mp 124°-125.5° C.). The total yield is 16.7 g (19.0 g theor., 88%).

Workup

  1. customwarms to ca 50° C.
  2. temperatureis maintained at this temperature
  3. customfor 5 hours
  4. additionThe reaction is poured onto ice water
  5. extractionextracted with diethyl ether (3×)
  6. extractionextracted with diethyl ether (3×)
  7. extractionThe combined ethereal layers from the second extraction
  8. washare washed with saturated aqueous NaCl
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo
  11. customto give an oil
  12. customCrystallizing from diethyl ether/pentane
  13. customgives 14.0 g of a first crop (mp 125°-126° C.) and 2.7 g as a second crop (mp 124°-125.5° C.)

Sources & evidence

ORD record
ord-3db5080530f441dc9a30fa6f8a2b7a13
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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