Bromide ion → 2-Allylphenol

反応式

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Br-].CCO[CH2:14][CH3:15].[CH3:16]N(C=O)C>>[CH2:16]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[OH:7])[CH:14]=[CH2:15]

参加物

反応物 5

HCID 259Bromide ion

HCID 996Phenol

HCID 3283Diethyl Ether2 回

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

生成物 1

HCID 156242-Allylphenol

実験手順

Phenol 25 may be treated with NaH in DMF and then alkylated with an allylic bromide to give ether 30. Claisen rearrangement of 30 under thermal conditions gives ortho-allyl phenol 31. Oxidation of the double bond in 31 with OsO4/NMO followed by cleavage with NaIO4 provides the lactol 32. Jones oxidation then provides lactone 33.