4-Benzyloxy-7-hydroxycoumarin → 7-(3-[4-Acetylphenyl]propoxy)-4-benzyloxycoumarin

HRID 2050162Notes

Reaction equation

HRID 2050162 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[O:12][C:11](=[O:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32]Br)=[CH:26][CH:25]=1)(=[O:23])[CH3:22]>CCO>[C:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][O:19][C:15]2[CH:14]=[C:13]3[C:18]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:10][C:11](=[O:20])[O:12]3)=[CH:17][CH:16]=2)=[CH:26][CH:25]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 134084074-Benzyloxy-7-hydroxycoumarinHCID 148170351-(4-Acetylphenyl)-3-bromopropane

Product 1

HCID 203314487-(3-[4-Acetylphenyl]propoxy)-4-benzyloxycoumarinYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Alkylation of 4-benzyloxy-7-hydroxycoumarin (2.68; 0.01 mole) with 1-(4-acetylphenyl)-3-bromopropane (2.41g; 0.01 mole) as described in example 45 gave 3.28g (77%) of title compound of m.p. (EtOH) 117°νmax (mull) 1725, 1682, 1620cm-1 ; τ(DMSO) 7.92 (2H, m); 7.48(3H, s); 7.18 (2H, m); 5.94(2H, t, J 6.4Hz); 6.69(2H, s); 6.16 (1H,s); 3.17-2.00(12H,m). (Found; C, 75.14; H, 5.52; C21H24O5 requires; C, 75.68; H, 5.65%

Sources & evidence

ORD record
ord-54904ef47afc4a67be967240fd3cfa20
Source dataset
uspto-grants-1980_04
Patent number
US04200577

Reaction notes

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