Hydroquinone → Monobenzone

HRID 729104Notes

Reaction equation

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

Participants

Reactant 2

HCID 785Hydroquinone

HCID 7498Benzyl Bromide

Product 1

HCID 7638Monobenzone

Procedure

Benzylbromide and hydroquinone are reacted to obtain 4-benzyloxyphenol (i),which is reacted with optical active perfluoro-2-(perfluoroalkoxy) propionic chloride in pyridine as a solvent to obtain 4-benzyloxyphenyl-perfluoro-2-(Perfluoroalkoxy) propionate (ii), which is then subjected to the hydrogenation in the presence of a palladium/carbon catalyst to obtain 4-hydroxyphenyl-perfluoro-2-(perfluoropropoxy) propionate (iii), which is reacted to 4-alkyloxybenzoic acid and thionyl chloride in pyridine as a solvent to obtain an objective optically active compound, 4-[perfluoro-2-(perfluoropropoxy)propionyloxy]phenyl4'-n-octyloxybenzoate.

Sources & evidence

ORD record: ord-9ee57721a9fe4f8d9190257b04835056
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05051527

Reaction notes

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