4-Cyclopentyloxydibenzo[b,d]furan-1-carbaldehyde → 4-Hydroxy dibenzo[b,d]furan-1-carbaldehyde

HRID 1293435Notes

Reaction equation

HRID 1293435 reaction equation
C1([O:6][C:7]2[C:12]3[O:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[C:11]=3[C:10]([CH:20]=[O:21])=[CH:9][CH:8]=2)CCCC1>Br.C(O)(=O)C>[OH:6][C:7]1[C:12]2[O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:11]=2[C:10]([CH:20]=[O:21])=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 442251954-Cyclopentyloxydibenzo[b,d]furan-1-carbaldehyde

Product 1

HCID 442251964-Hydroxy dibenzo[b,d]furan-1-carbaldehyde

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

Intermediate 18 was heated in HBr (30-33%) in glacial acetic acid (25 ml) at 50° C. for 7-8 h The reaction contents were poured in ice-water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, and extracted with 10% sodium hydroxide (3×25 ml) solution. The aqueous layer was acidified with conc. HCl to give a white precipitate which was filtered and air dried to obtain the crude product as a white solid (3.2 gm).

Workup

  1. customThe reaction contents
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate
  4. extractionextracted with 10% sodium hydroxide (3×25 ml) solution
  5. customto give a white precipitate which
  6. filtrationwas filtered
  7. customair dried

Sources & evidence

ORD record
ord-546a47de5d0845de85c1bfa0f309df12
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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