Bromide ion → 2-Allylphenol

HRID 325174

Reaction equation

HRID 325174 reaction equation
[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]

Participants

6

Reactant 5

HCID 259Bromide ionHCID 996PhenolHCID 3283Diethyl Ether2×HCID 6228DimethylformamideHCID 24758Sodium hydride

Product 1

HCID 156242-Allylphenol

Procedure

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.

Sources & evidence

ORD record
ord-b7d538998ef745339debbef27317b340
Source dataset
uspto-grants-2001_04
Patent number
US06222048B1

Linked notes

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