Ethyl Acetate → 4-t-Butyl-5-hydroxy-2-methylbenzofuran

HRID 2119686Notes

Reaction equation

HRID 2119686 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH:17]=O)=[CH:14][C:13]=2[C:19]=1[C:20]([CH3:23])([CH3:22])[CH3:21])C1C=CC=CC=1.C(OCC)(=O)C.[H][H]>[Pd].C(O)(=O)C>[C:20]([C:19]1[C:13]2[CH:14]=[C:15]([CH3:17])[O:16][C:12]=2[CH:11]=[CH:10][C:9]=1[OH:8])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 234428795-Benzyloxy-4-t-butyl-2-formylbenzofuranHCID 178418361HCID 178418361, compound

Product 1

HCID 234428664-t-Butyl-5-hydroxy-2-methylbenzofuranYield 17%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1.0 g of 5-benzyloxy-4-t-butyl-2-formylbenzofuran in a mixed solvent of 50 ml of ethyl acetate and 2 ml of acetic acid was vigorously stirred with 1.0 g of 10% palladium on carbon for 20 hours in a hydrogen atmosphere. After the palladium on carbon was filtered out, the filtrate was concentrated and the concentrate was purified by silica gel column chromatography (in n-hexane containing 20% ethyl acetate) to give 0.11 g of 4-t-butyl-5-hydroxy-2-methylbenzofuran as a white crystal (yield 17%).

Workup

  1. filtrationAfter the palladium on carbon was filtered out
  2. concentrationthe filtrate was concentrated
  3. customthe concentrate was purified by silica gel column chromatography (in n-hexane containing 20% ethyl acetate)

Sources & evidence

ORD record
ord-098e2f106f42436baf4e25e204d44084
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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