Methyl 3,5-bis(methoxymethoxy)benzoate → 3,5-Bis(methoxymethoxy)benzylalcohol

HRID 1643692Notes

Reaction equation

HRID 1643692 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH2:11][O:12][CH3:13])[CH:7]=[C:6]([O:14][CH2:15][O:16][CH3:17])[CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:13][O:12][CH2:11][O:10][C:8]1[CH:9]=[C:4]([CH2:3][OH:2])[CH:5]=[C:6]([O:14][CH2:15][O:16][CH3:17])[CH:7]=1

Participants

4

Reactant 2

HCID 10106435Methyl 3,5-bis(methoxymethoxy)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 104437513,5-Bis(methoxymethoxy)benzylalcoholYield 92.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3,5-bis-methoxymethoxy-benzoic acid methyl ester (220a) (350 g, 1.37 mol) in THF (1.8 L) was added portion wise LiAlH4 (62 g, 1.64 mol) at 0° C. The mixture was stirred at 0° C. for another 1 hr. TLC (EtOAc/petroleum ether=1/2) showed that the reaction was complete. The reaction was quenched with 2 N aqueous NaOH. The mixture was filtered through Celite. The filtrate was dried over Na2SO4 and concentrated to give the title compound (290 g, 76%) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 6.70 (d, 2H), 6.64 (d, 1H), 5.22 (s, 4H), 4.61 (s, 2H), 3.46 (s, 6H).

Workup

  1. customThe reaction was quenched with 2 N aqueous NaOH
  2. filtrationThe mixture was filtered through Celite
  3. dry with materialThe filtrate was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4effce924a244283b8623c4c7c80d7cf
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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