4-Hydroxybenzophenone → {4-[(But-2-en-1-yl)oxy]phenyl}(phenyl)methanone

HRID 2292194Notes

Reaction equation

HRID 2292194 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](Br)[CH:17]=[CH:18][CH3:19].CC(C1C=C(C=CC=1O)C(C1C=CC=CC=1)=O)C=C>>[CH2:16]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:14][CH:15]=1)[CH:17]=[CH:18][CH3:19]

Participants

4

Reactant 3

HCID 143474-HydroxybenzophenoneHCID 1224142-Butene, 1-bromo-HCID 14089150HCID 14089150, compound

Product 1

HCID 53863387{4-[(But-2-en-1-yl)oxy]phenyl}(phenyl)methanone

Procedure

4-crotyloxybenzophenone was prepared from 4-hydroxybenzophenone and crotyl bromide using the procedure of Example 23. Through Claisen rearrangement it was converted into 3-(α-methyl-allyl)-4-hydroxybenzophenone. The crude product (10.1 g) was acylated (procedure of Example 1) and purified by chromatography (40:60 hexane-methylene chloride on silica gel) to produce 12.25 g (91%) of oil.

Workup

  1. custompurified by chromatography (40:60 hexane-methylene chloride on silica gel)

Sources & evidence

ORD record
ord-f9f0e0628dc8417a9036686f221bf554
Source dataset
uspto-grants-1989_01
Patent number
US04801610

Reaction notes

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