Process for preparing 3-chloro-2-vinylphenylsulfonates

A process for preparing one or more 3-chloro-2-vinylphenylsulfonate derivatives of formula (I),

• wherein
• R1 represents C1-C6-alkyl, phenyl, 4-methylphenyl or benzyl,
• comprising
• (A) reacting 3-chloro-2-methylphenol of formula (II)
• with a compound of formula (III),
• wherein
• Hal represents F or Cl and
• R2 represents F, Cl, F3C, F2HC, Cl3C, Cl2HC, ClH2C or Cl3CO,
• or reacting the 3-chloro-2-methylphenol of formula (II)
• with an acid derivative of formula (IV),
• wherein
• R3 and R4 independently from each other represent F3C, F2HC, Cl3C, Cl2HC, or ClH2C,
• or reacting the 3-chloro-2-methylphenol of formula (II)
• with triphosgene
• in the presence of a base and a solvent
• to form a compound of formula (V)
• wherein
• R5 represents F, Cl, CCl3, CHCl2, CH2Cl, CF3, CHF2 or 3-chloro-2-methylphenoxy;
• (B) reacting one or more compounds of formula (V) with a chlorinating agent to produce one or more compounds of formula (VI)
• wherein
• R6 represents F, Cl, CCl3, CHCl2, CH2Cl, CF3, CHF2 or 3-chloro-2-(dichloromethyl)phenoxy;
• (C) reacting the compound of formula (VI) under acidic conditions or at elevated temperature in water to produce 2-chloro-6-hydroxybenzaldehyde (VII)
• (D) reacting the compound of formula (VII) or an alkaline or alkaline earth metal salt thereof in the presence of a solvent with a compound of formula (VIII)
• Me-Q (VIII),
• wherein
• Q represents Li, Na, K, MgCl, MgBr or, MgI
• to produce 3-chloro-2-(1-hydroxyethyl)phenol (IX)
• and
• (E) forming 3-chloro-2-vinylphenylsulfonate derivatives of formula (I) by reacting the compound of formula (IX) in the presence of a base with a compound of formula (X)
• R1—SO2—W (X),
• wherein
• W represents F, Cl, Br or OSO2R1.