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

HRID 1505092Notes

Reaction equation

HRID 1505092 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 3 h 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, 1 H), 6.54 (s, 1 H), 5.96 (s, 2 H), 4.57 (s, 2 H), 3.90 (s, 3 H).

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-40e59cb249864566ae36b67857eaab0c
Source dataset
uspto-grants-2015_12
Patent number
US09216969B2

Reaction notes

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