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

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

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.