4-formyl-2,6-dimethoxyphenyl acetate → HCID 68625269, compound

HRID 722093Notes

Reaction equation

HRID 722093 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][C:12](=[O:14])[CH3:13])=[C:5]([O:15][CH3:16])[CH:4]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]([O:15][CH3:16])[C:6]([O:11][C:12](=[O:14])[CH3:13])=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

4

Reactant 2

HCID 6881894-formyl-2,6-dimethoxyphenyl acetateHCID 4311764Sodium borohydride

Product 1

HCID 68625269HCID 68625269, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of acetic acid 4-formyl-2,6-dimethoxy-phenyl ester (25 mmol) in MeOH (100 mL) was treated with NaBH4 (1 equiv.) at 0° C. for 15 min. After quenching with acetone and evaporating the solvent, work-up (CH2Cl2) and evaporation gave the title compound as a white solid (85% yield). Rf (in EtOAc/Hexane 1:1): 0.5. 1H-NMR (CDCl3): δ 6.66 (s, 1H), 4.68–4.70 (d, 2H), 3.85 (s, 3H), 2.36 (s, 3H), 1.74 (t, 1H).

Workup

  1. customAfter quenching with acetone
  2. customevaporating
  3. customthe solvent, work-up (CH2Cl2) and evaporation

Sources & evidence

ORD record
ord-d15d01cccb924a2aa5bdbaf84f7d44f9
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

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