Sodium Hydroxide → Trolox

HRID 1434908Notes

Reaction equation

HRID 1434908 reaction equation
[OH:1][C:2]1[C:3]([CH3:19])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:18])([C:14]([O:16]C)=[O:15])[CH2:6][CH2:5]2.[OH-].[Na+].S([O-])(O)(=O)=O.[K+]>CO.O>[OH:1][C:2]1[C:3]([CH3:19])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:18])([C:14]([OH:16])=[O:15])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 10171518HCID 10171518, compound

Product 1

HCID 40634Trolox

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Into a 2000-L reactor provided with glass lining, methyl 6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylate (137.3 kg) obtained in Example 6 was placed and dissolved in methanol (137.3 kg). A solution containing water (411 kg) and sodium hydroxide (27 kg) was added dropwise thereto over two hours, whereby hydrolysis was performed at 80° C. for two hours. The hydrolyzed mixture was neutralized with a solution of potassium hydrogensulfate (91.9 kg) dissolved in water (411.9 kg) at 80° C. for two hours. The reaction mixture was centrifuged, and the obtained crystals were dried by means of a conical drier, to thereby yield 6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid (130.2 kg) in the form of white powder. Reaction scores on the basis of 6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylate and chemical purity which was determined through high-performance liquid chromatography (HPLC) were found to be as follows:

Workup

  1. additionwas added dropwise
  2. customwhereby hydrolysis
  3. waitwas performed at 80° C. for two hours
  4. customthe obtained crystals were dried by means of a conical drier
  5. customReaction scores on the basis of 6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylate and chemical purity which

Sources & evidence

ORD record
ord-a7d2ee45539f476c87f8c37ffee1a737
Source dataset
uspto-grants-2009_11
Patent number
US07615650B2

Reaction notes

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