Pyridinium chloride → 1-[2-(4-Hydroxynaphthalen-1-yl)-1-benzofuran-3-yl]ethan-1-one

HRID 1287930Notes

Reaction equation

HRID 1287930 reaction equation
[C:1]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([O:23]C)=[CH:15][CH:14]=1)(=[O:3])[CH3:2].Cl.N1C=CC=CC=1>>[C:1]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([OH:23])=[CH:15][CH:14]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 123270011-[2-(4-Methoxynaphthalen-1-yl)-1-benzofuran-3-yl]ethan-1-one

Product 1

HCID 215070471-[2-(4-Hydroxynaphthalen-1-yl)-1-benzofuran-3-yl]ethan-1-one

Procedure

A mixture of 13.8 g. (0.044 mol.) of 3-acetyl-2-(4-methoxynaphthyl)benzofuran and 100 g. of pyridine hydrochloride was heated at 185° for 4.5 hours. The hot reaction mixture was poured into an ice-dilute hydrochloric acid mixture and the aqueous solution was extracted with ether. The extract was dried (MgSO4) and evaporated to give 3-acetyl-2-(4-hydroxynaphthyl)benzofuran, m.p. 212°-216°.

Workup

  1. additionA mixture of 13.8 g
  2. extractionthe aqueous solution was extracted with ether
  3. dry with materialThe extract was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-21a39043091e41808d9d8a288306ddf3
Source dataset
uspto-grants-1976_10
Patent number
US03985896

Reaction notes

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