Water → (7-Methoxy-1,3-benzodioxol-5-yl)methanol

HRID 1442714Notes

Reaction equation

HRID 1442714 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[C:5]([C:12](OC)=[O:13])[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[C:5]([CH2:12][OH:13])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 601780Methyl 3,4-methylenedioxy-5-methoxybenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 602667(7-Methoxy-1,3-benzodioxol-5-yl)methanolYield 98.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 7-methoxybenzo[d][1,3]dioxole-5-carboxylate (13.9 g, 0.040 mol) in THF (100 mL) was added LiAlH4 (3.1 g, 0.080 mol) in portions at room temperature. The mixture was stirred for 3H at room temperature. The reaction mixture was cooled to 0° C. and treated with water (3.1 g) and NaOH (10%, 3.1 mL) successively. The slurry was filtered off and washed with THF. The combined filtrates were evaporated under reduced pressure to give (7-methoxy-benzo[d][1,3]dioxol-5-yl)methanol (7.2 g, 52%). 1H NMR (400 MHz, CDCl3) δ 6.55 (s, 1H), 6.54 (s, 1H), 5.96 (s, 2H), 4.57 (s, 2H), 3.90 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationThe slurry was filtered off
  3. washwashed with THF
  4. customThe combined filtrates were evaporated under reduced pressure

Sources & evidence

ORD record
ord-3b2f92d493da4cfb8f88d9cb94f0258b
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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