Reaktion #416042

ord-b2287f90acd5401cb947eba975093cd9

Reaktionsgleichung

CC(=O)CCc1c(C)c(OC(C)=O)c(C)c(C)c1OC(C)=O
(±)-4-(2,5-diacetoxy-3,4,6-trimethyphenyl)butan-2-one
COP(=O)(O)C(C)(C)C(=O)[O-]
trimethylphosphonoacetate
→
Cc1c(C)c2c(c(C)c1O)CCC(C)(CC(=O)O)O2
(±)-6-hydroxy-2,5,7,8-tetramethylchroman-2-acetic acid

Edukte

CC(=O)CCc1c(C)c(OC(C)=O)c(C)c(C)c1OC(C)=O
(±)-4-(2,5-diacetoxy-3,4,6-trimethyphenyl)butan-2-one
COP(=O)(O)C(C)(C)C(=O)[O-]
trimethylphosphonoacetate

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe crude (±)-methyl 5-(2,5-diacetoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenoate thus obtained, upon saponification with base as in Example 6

Vorschrift

By the procedure described in Example 6, (±)-4-(2,5-diacetoxy-3,4,6-trimethyphenyl)butan-2-one was treated with the anion from trimethylphosphonoacetate. The crude (±)-methyl 5-(2,5-diacetoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenoate thus obtained, upon saponification with base as in Example 6, yielded (±)-6-hydroxy-2,5,7,8-tetramethylchroman-2-acetic acid as a light tan powder, m.p. 169°-171.5°.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04018799uspto-grants-1977_04