Hydroquinone → 3,4-Dihydro-2H-1-benzopyran-6-ol

HRID 63804

Reaction equation

HRID 63804 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:9]1([CH:16]=[CH:15][C:13]([OH:14])=[CH:12][CH:11]=1)[OH:10].[CH3:17][C:18](O)(CCCC(C)CCCC(C)CCCC(C)C)[CH:19]=C>[Cl-].[Cl-].[Zn+2]>[O:10]1[C:9]2[C:16](=[CH:15][C:13]([OH:14])=[CH:12][CH:11]=2)[CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 10453IsophytolHCID 24489Sodium Dithionite

Product 1

HCID 151223383,4-Dihydro-2H-1-benzopyran-6-ol

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

2,6-dimethylquinone 111 is reduced with sodium dithionite to the hydroquinone 112, which is then reacted with 3,7,11,15-tetramethyl-3-hydroxy-1-hexadecene 113 and ZnCl2 to form the 6-chromanol 114. Conversion to the protected intermediate 115 is followed by bromination with Br2 and silver trifluoroacetate to form the bromide 116. Finally, 116 can be deprotected and oxidized with ceric ammonium nitrate (CAN) to yield 117.

Sources & evidence

ORD record
ord-a4c73b0460b94898a0a84e03a3b86891
Source dataset
uspto-grants-2016_09
Patent number
US09447006B2

Linked notes

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