Potassium Sodium Tartrate → HCID 58438856, compound

HRID 217449Notes

Reaction equation

HRID 217449 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH3:22])=[CH:16][C:15]=2[O:23][CH3:24])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[OH:5][CH2:4][C:3]1[CH:8]=[CH:9][C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH3:22])=[CH:16][C:15]=2[O:23][CH3:24])=[CH:11][C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 58438701HCID 58438701, compound

Product 1

HCID 58438856HCID 58438856, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-hydroxy-4-[(2-methoxy-4-propylphenoxy)methyl]benzoate (300 mg) was dissolved in THF (15 mL). To the reaction liquid was added LAH (103.4 mg) at 0° C., followed by warming from 0° C. to 25° C. and then stirring for 3 hours. To the reaction liquid was added a saturated aqueous Rochelle salt solution (30 mL), followed by extraction with EtOAc (30 mL) three times. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 80:20) to obtain 2-(hydroxymethyl)-5-[(2-methoxy-4-propylphenoxy)methyl]phenol (245.2 mg) as a white solid.

Workup

  1. customTo the reaction liquid
  2. temperatureby warming from 0° C. to 25° C.
  3. customTo the reaction liquid
  4. extractionfollowed by extraction with EtOAc (30 mL) three times
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 80:20)

Sources & evidence

ORD record
ord-3c471cd341974086a7610e2ef556ac43
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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