Aluminium lithium hydride → (3-(Hydroxymethyl)-5-methoxyphenyl)methanol

HRID 2253724Notes

Reaction equation

HRID 2253724 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:14]([O-])=[O:15])[CH:6]=[C:7]([CH:13]=1)[C:8](OCC)=[O:9].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC>[OH:9][CH2:8][C:7]1[CH:13]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([CH2:14][OH:15])[CH:6]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86747067Methyl,methyl 5-methoxyisophthalate

Product 1

HCID 4114928(3-(Hydroxymethyl)-5-methoxyphenyl)methanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.00 g (22.32 mmoles) of methyl,methyl 5-methoxyisophthalate in 100 ml dry THF is added dropwise, maintaining a gentle reflux, 67 ml (66.96 mmoles) of a 1M solution of lithium aluminum hydride in Et2O. After addition the reaction mixture is stirred for 1 hour and is then quenched with saturated NH4Cl. The reaction mixture is then extracted with Et2O (3 times). The Et2O layers are combined, washed with brine, dried with MgSO4, filtered and concentrated down in vacuo to yield 1,3-di-(hydroxymethyl)-5-methoxybenzene which is used directly in the next step.

Workup

  1. additionAfter addition the reaction mixture
  2. customis then quenched with saturated NH4Cl
  3. extractionThe reaction mixture is then extracted with Et2O (3 times)
  4. washwashed with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated down in vacuo

Sources & evidence

ORD record
ord-73af88ba3a93488ca2e5a9dc2d63d393
Source dataset
uspto-grants-1993_08
Patent number
US05232948

Reaction notes

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