Aromatic compounds from furanics

A method of preparing an optionally substituted compound comprising formula (I):

• wherein:
• G is OH CHO, or CO2H, an ether thereof, an ester thereof, or an anhydride thereof, the method comprising:
• (i) reacting a biomass-derived compound comprising formula (II) with a compound comprising formula (III):
• wherein:
• the compound of formula (II) is optionally substituted at one or more of the 3, 4, or 5 position with a C1-C20 hydrocarbyl or with F, Cl, Br, I, CH2F, CH2Cl, CH2Br, CH2I, CN, NO2, CHO, CO2H or ester thereof, CH2NH2 or secondary, tertiary, or quaternary amine or amide thereof, or CH2OH or ester or ether thereof;
• wherein said C1-C20 hydrocarbyl is optionally substituted is one or more of F, Cl, Br, I, CH2F, CH2Cl, CH2Br, CH2I, CN, NO, CHO, CO2H or ester thereof, CH2NH2 or secondary, tertiary, or quaternary amine or amide thereof, or CH2OH or ester or ether thereof;
• X is O and z is 0, or
• X is N and z is 1,
• R1 is a C1-C20 hydrocarbyl, optionally substituted with one or more phenyl, F, Cl, Br, I, CH2F, CH2Cl, CH2Br, CH2I, CN, NO2, CHO, CO2H or ester thereof, CH2NH2 or secondary, tertiary, or quaternary amine or amide thereof, or CH2OH or ester or ether thereof, and
• R2 is hydrogen or a C1-C20 hydrocarbyl, optionally substituted with one or more phenyl, F, Cl, Br, I, CH2F, CH2Cl, CH2Br, CH2I, CN, NO2, CHO, CO2H or ester thereof, CH2NH2 or secondary, tertiary, quaternary amine or amide thereof, or CH2OH or ester or ether thereof,
• to give an optionally substituted compound comprising formula (IV):
• (ii) reacting the optionally substituted compound comprising formula (IV) with a C2-C12 alkene or C2-C12 alkyne in the presence of a Lewis and/or Brønsted acid catalyst to give an optionally substituted compound comprising formula (V):
• (iii) hydrolyzing said optionally substituted compound comprising formula (V) to yield the optionally substituted compound comprising formula (I), wherein G is CHO, and
• (iv-a) optionally decarbonylating the product of step (iii) to provide the optionally substituted compound comprising formula (I), wherein G is OH, or
• (iv-b) optionally oxidizing the product of step (iii) to yield the optionally substituted compound comprising formula (I), wherein G is CO2H, and
• (v) optionally converting the optionally substituted compound comprising formula (I), wherein G is OH, CHO, or CO2H to the ether, ester, or anhydride thereof.