1,2-Dichlorobenzene → 2,4-Dihydroxy-3-allylbenzophenone

Reaction equation

C([O:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[C:7]([OH:19])[CH:6]=1)C=C.Cl[C:21]1[CH:26]=CC=C[C:22]=1Cl>>[OH:19][C:7]1[C:6]([CH2:26][CH:21]=[CH2:22])=[C:5]([OH:4])[CH:18]=[CH:17][C:8]=1[C:9]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:10]

Participants

Reactant 2

HCID 72391,2-Dichlorobenzene

HCID 756894-Allyloxy-2-hydroxybenzophenone

Product 1

HCID 219109812,4-Dihydroxy-3-allylbenzophenone

Procedure

Commercially available 4-allyloxy-2-hydroxybenzophenone (15 g) was rearranged by heating under reflux in ortho-dichlorobenzene (60 mL) for 26 hours. The product was isolated by dilution of the reaction mixture with 5 volumes hexanes to give a crystalline product as fine needles.

Workup

temperatureby heating

Sources & evidence

ORD record: ord-83d069dc05c04271afbe84952104b3b2
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091230B2

Reaction notes

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