4-Hydroxybenzophenone → [4-Hydroxy-3-(prop-2-en-1-yl)phenyl](phenyl)methanone

HRID 2292193Notes

Reaction equation

[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:16](OC1C=CC(C(C2C=CC=CC=2)=O)=CC=1)[CH:17]=[CH2:18]>>[CH2:18]([C:15]1[CH:14]=[C:5]([CH:4]=[CH:3][C:2]=1[OH:1])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])[CH:17]=[CH2:16]

Participants

Reactant 2

HCID 143474-Hydroxybenzophenone

HCID 2579104-Allyloxybenzophenone

Product 1

HCID 257912[4-Hydroxy-3-(prop-2-en-1-yl)phenyl](phenyl)methanoneYield 47%

Procedure

4-hydroxybenzophenone (25 g) was converted to 4-allyloxybenzophenone (29.2 g, yellow solid) by the procedure of Example 23. Claisen rearrangement using that procedure gave 13.5 g (47%) of desired 3allyl-4-hydroxybenzophenone, the balance being recovered. Finally, acylation of 3-allyl-4-hydroxybenzophenone (5.9 G) according to general procedure of Example 1 produced 6.9 g (86%) of product as yellow solid.

Sources & evidence

ORD record: ord-64e158f082a94f37b08cdc212ec780e4
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04801610

Reaction notes

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