2-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1) → HCID 68499938, compound

HRID 1176286Notes

Reaction equation

HRID 1176286 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([CH3:15])[O:14][CH2:13][CH2:12][CH2:11][O:10]1.[H-].C([Al+]CC(C)C)C(C)C.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([O:10][CH2:11][CH2:12][CH2:13][OH:14])[CH3:15]

Participants

6

Reactant 3

HCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 21225700DiisobutylaluminumhydrideHCID 68499187HCID 68499187, compound

Product 1

HCID 68499938HCID 68499938, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The solution of 61.9 g of 2-(2-methoxyphenyl)-2-methyl-[1,3]dioxane in 450 ml of toluene is cooled to 0° C. with stirring and admixed at 0-10° C. with 487 ml of diisobutylaluminum hydride (1.5M in toluene) over 1 hour. The mixture is stirred over 2.5 hours and subsequently poured onto the stirred solution of 382 g of citric acid monohydrate in 2 l of water. The organic phase is removed and the water phase extracted with tert-butyl methyl ether (1 l). The organic phases are washed with brine (1 l), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.12 (1:2 EtOAc-heptane); Rt=3.56.

Workup

  1. stirringThe mixture is stirred over 2.5 hours
  2. customThe organic phase is removed
  3. extractionthe water phase extracted with tert-butyl methyl ether (1 l)
  4. washThe organic phases are washed with brine (1 l)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1a94dc66067446468156d03d590aae27
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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