(R)-2-HYDROXY-2-METHYL(4-CHLOROBENZENE)ACETIC ACID synthesis

Yield:-

Steps:

Multi-step reaction with 4 steps
1.1: cyclohexane / 1 h / 65 - 80 °C / Dean-Stark; Inert atmosphere
2.1: (1S)-(+)-10-camphorsulfonic acid / toluene / 6.5 h / 0 - 5 °C
3.1: n-butyllithium; lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 - -10 °C / Inert atmosphere
3.2: 2.58 h / 0 - 5 °C / Inert atmosphere
4.1: sodium hydroxide / methanol / 1 h / 0 - 20 °C

References:

Misaki, Tomonori;Ureshino, Satoko;Nagase, Ryohei;Oguni, Yumiko;Tanabe, Yoo [Organic Process Research and Development,2006,vol. 10,# 3,p. 500 - 504]