Water → 7-Hydroxy-2-methylbenzo[b]furan-4-carbaldehyde

HRID 548992Notes

Reaction equation

HRID 548992 reaction equation
C[O:2][C:3]1[C:8]2[O:9][C:10]([CH3:12])=[CH:11][C:7]=2[C:6]([CH:13]=[O:14])=[CH:5][CH:4]=1.CN(P(N(C)C)(N(C)C)=O)C.O>C1(C)C=CC=CC=1>[OH:2][C:3]1[C:8]2[O:9][C:10]([CH3:12])=[CH:11][C:7]=2[C:6]([CH:13]=[O:14])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12679HexamethylphosphoramideHCID 110415447-Methoxy-2-methyl-1-benzofuran-4-carbaldehyde

Product 1

HCID 824109927-Hydroxy-2-methylbenzo[b]furan-4-carbaldehydeYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a freshly prepared solution of sodium-4-methyl benzene thiolate (prepared from 42 g of 4-methyl benzene thiol and 14 g of sodium hydroxide) in toluene (700 mL) was added 7-methoxy-2-methylbenzo[b]furan-4-carboxaldehyde (50.0 g) at reflux. Then HMPA (62.0 g) was added slowly and reaction mixture was stirred at the same temperature for 4-5 hr. reaction mixture was then bring to 50-60° C., water (500 mL) was added and layers were separated. The aqueous layer was acidified (pH 4-5). The solid separated was filtered, washed with water (3×200 mL) and dried to get light yellow solid product (44.0 g).

Workup

  1. temperatureat reflux
  2. customreaction mixture
  3. customreaction mixture
  4. customwas then bring to 50-60° C.
  5. customlayers were separated
  6. customThe solid separated
  7. filtrationwas filtered
  8. washwashed with water (3×200 mL)
  9. customdried

Sources & evidence

ORD record
ord-b13acf001e74480dad7a496686b6ef82
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

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