Benzyl Chloride → 4-Benzyloxy-7-hydroxycoumarin

HRID 2057592Notes

Reaction equation

HRID 2057592 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[O:5][C:4](=[O:13])[CH:3]=1.[H-].[Na+].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([O:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[O:5][C:4](=[O:13])[CH:3]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 546796304,7-Dihydroxycoumarin

Product 1

HCID 134084074-Benzyloxy-7-hydroxycoumarinYield 23.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4,7-dihydroxycoumarin (1.78 g, 0.01 mole) in dry DMF (7.5 ml) was stirred during the addition of 100% sodium hydride (0.24 g, 0.01 mole) and the mixture stirred for 1 hour at 100°. A solution of benzyl chloride (1.27 g, 0.01 mole) in dry DMF (1 ml) was added dropwise and stirring continued at 100° for a further 4 hours. After removal of the solvent in vacuo water was added and the oily solid which precipitated was separated. Recrystallisation from ethanol gave 0.623 g (23%) of title compound of m.p. 234° νmax (mull) 3150, 3050, 1710, 1630 cm-1, τ(DMSO) 4.67 (2H, s); 4.19 (1H, s); 3.28 (1H near s); 3.20 (1H, d.d., J 2.0 Hz; 5.0 Hz) 2.66-2.26 (6H, m), 1 low field broad exchangeable proton. (Found, C, 71.51; H, 4.70; C16H12O4 requires; C, 71.64; H, 4.51%).

Workup

  1. stirringstirring
  2. waitcontinued at 100° for a further 4 hours
  3. customAfter removal of the solvent in vacuo water
  4. additionwas added
  5. customthe oily solid which precipitated
  6. customwas separated
  7. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-ceb844ac6aec48b1a3cfe3bea4508836
Source dataset
uspto-grants-1980_07
Patent number
US04211791

Reaction notes

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