Water → 3(2H)-Benzofuranone, 6-(phenylmethoxy)-

HRID 1376898Notes

Reaction equation

HRID 1376898 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[CH2:18]([O:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2357176-Hydroxy-3-coumaranone

Product 1

HCID 106337743(2H)-Benzofuranone, 6-(phenylmethoxy)-Yield 95.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-hydroxy-3-oxo-2,3-dihydrobenzofuran of Example 10(a) (32 kg, 213 moles) in DMF (192 L) was added potassium carbonate (31.0 kg, 224 moles). After stirring for 5 min. at room temperature, benzyl bromide (45.2 kg, 264 moles) was added and the resulting mixture was stirred for 2 hours at room temperature. The mixture was poured into water (651 L), stirred for 30 minutes and the product collected by centrifugation. The crude solid was washed with water (580 L), 80% ethanol (100 L) and dried under vacuum to afford the desired product (49.1 kg, 95%) which was used without any further purification.

Workup

  1. stirringthe resulting mixture was stirred for 2 hours at room temperature
  2. stirringstirred for 30 minutes
  3. customthe product collected by centrifugation
  4. washThe crude solid was washed with water (580 L), 80% ethanol (100 L)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0e9ef87909fa42cb82849705683db1c1
Source dataset
uspto-grants-1997_09
Patent number
US05663368

Reaction notes

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