4-Hydroxybenzaldehyde → HCID 19925663, compound

HRID 1647501Notes

Reaction equation

HRID 1647501 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([C:20]1[O:21][C:22]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][C:23]=2[CH:24]=1)=[O:19].Cl>CN(C)C=O>[CH:29]([C:26]1[CH:27]=[CH:28][C:22]2[O:21][C:20]([C:18](=[O:19])[CH2:17][O:1][C:2]3[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=3)=[CH:24][C:23]=2[CH:25]=1)([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 15337971HCID 15337971, compound

Product 1

HCID 19925663HCID 19925663, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

p-Hydroxybenzaldehyde (12.2 g) was dissolved in 200 ml of N,N-dimethylformamide, 13.8 g of anhydrous potassium carbonate was added and, with stirring at room temperature, 28.1 g of 2-bromoacetyl-5-isopropylbenzofuran was added thereto within 30 minutes. The mixture was stirred at room temperature for 2 hours more. The reaction mixture was poured into aqueous solution of hydrochloric acid and the resulting crystals were collected by filtration and washed with water. The crystals were then dissolved in ethyl acetate, the solution was washed with water and the ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated in vacuo whereupon the residue was crystallized. Ether was added to the crystals and then collected by filtraton to give 18.1 g of crystals.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours more
  2. filtrationthe resulting crystals were collected by filtration
  3. washwashed with water
  4. dissolutionThe crystals were then dissolved in ethyl acetate
  5. washthe solution was washed with water
  6. dry with materialthe ethyl acetate layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo whereupon the residue
  8. customwas crystallized
  9. additionEther was added to the crystals
  10. customcollected by filtraton

Sources & evidence

ORD record
ord-1e030e5b9b2a4b1b8cff17d1c9e2a320
Source dataset
uspto-grants-1995_07
Patent number
US05432195

Reaction notes

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