Water → 7-Hydroxymethyl-2-phenylbenzofuran

HRID 1639024Notes

Reaction equation

HRID 1639024 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[OH:17][CH2:16][C:15]1[C:9]2[O:8][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:11][C:10]=2[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 142297062-Phenylbenzofuran-7-carboxylic acidHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 145149497-Hydroxymethyl-2-phenylbenzofuranYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

2-Phenylbenzofuran-7-carboxylic acid (40 g) is dissolved in tetrahydrofuran (300 ml) and the solution is added dropwise to a suspension of lithium aluminum hydride (19.12 g) in tetrahydrofuran (130 ml) under ice-cooling. After the mixture is stirred at 70° C. for 2 hours, water is added to the mixture to decompose excess lithium aluminum hydride and its complex. Insoluble materials are filtered off, and the filtrate is concentrated under reduced pressure to remove solvent. The residue is dissolved in ethyl acetate, and the solution is washed with water, dried and concentrated under reduced pressure to remove solvent. The residue is recrystallized from a mixture of ethyl acetate and n-hexane, whereby 7-hydroxymethyl-2-phenylbenzofuran (34.4 g) is obtained. Yield: 91%.

Workup

  1. temperaturecooling
  2. filtrationInsoluble materials are filtered off
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customto remove solvent
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washthe solution is washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto remove solvent
  10. customThe residue is recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-2a8118c18c3f4b96922df1c55f748ec8
Source dataset
uspto-grants-1989_11
Patent number
US04882340

Reaction notes

Loading…