1,4-Dichlorobenzene → Methyl 4-hydroxy-3-propylbenzoate

HRID 2294637Notes

Reaction equation

HRID 2294637 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH:12]1[C:17](Cl)=CC=C(Cl)[CH:13]=1>>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([CH2:13][CH2:12][CH3:17])[CH:5]=1

Participants

3

Reactant 2

HCID 46851,4-DichlorobenzeneHCID 7456Methylparaben

Product 1

HCID 11805593Methyl 4-hydroxy-3-propylbenzoate

Procedure

The synthesis begins with the allylation of readily available methyl-4-hydroxybenzoate (Scheme 1). The allylated phenol is then thermally rearranged in dichlorobenzene and subsequently hydrogenated to provide the desired Methyl-4-hydroxy-3-n-propylbenzoate in good overall yield. ##STR27##

Sources & evidence

ORD record
ord-f565139ad4a54453b845b6bd36afe5f1
Source dataset
uspto-grants-1997_11
Patent number
US05688974

Reaction notes

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