Methyl 3,4-methylenedioxy-5-methoxybenzoate → (7-Methoxy-1,3-benzodioxol-5-yl)methanol

HRID 2213934Notes

Reaction equation

HRID 2213934 reaction equation
[CH2:1]1[O:13][C:12]2[C:11]([O:14][CH3:15])=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][C:3]=2[O:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]1[O:13][C:12]2[C:11]([O:14][CH3:15])=[CH:10][C:5]([CH2:6][OH:7])=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 601780Methyl 3,4-methylenedioxy-5-methoxybenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 602667(7-Methoxy-1,3-benzodioxol-5-yl)methanolYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl ester 5 (11.9 g, 57 mmol) in THF (50 ml) was added (slowly) dropwise to a stirred grey suspension of lithium aluminum hydride (3.4 g, 90 mmol) in THF (50 ml) at 0° C. under Ar. After stirring for 3 h at rt, the suspension was cooled to 0° C. and the reduction terminated by careful addition of Na2SO4 (sat., aq) until effervescence ceased. The precipitate was collected and the filtrant dried and concentrated in vacuo to afford benzyl alcohol 6 (9.3 g, 91%) as a colorless powder, m.p. 66–67° C. (lit. mp 66–67° C., Pettit and Singh, 1987); 1H-NMR (300 MHz):1.59 (1H, bs, —OH), 3.91 (3H, s, —OCH3) 4.59 (2H, bs, —ArCH2O—), 5.97 (2H, s, —OCH2O—), 6.56 (2H, d, J=2.1 Hz, ArH).

Workup

  1. temperaturethe suspension was cooled to 0° C.
  2. customthe reduction terminated by careful addition of Na2SO4 (sat., aq) until effervescence
  3. customThe precipitate was collected
  4. customthe filtrant dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ef83cc12c194582a3e3b0fc88b1aa30
Source dataset
uspto-grants-2006_09
Patent number
US07105695B2

Reaction notes

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