Reaction #1158063

Reaction equation

HCl

NaOH

Methyl 5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl) methyl]-2-furoate

→

5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-2-furoic acid

Solvents

water

water

MeOH

Conditions

Workup

1. 1
   ExtractionThe crude product was extracted in to organic layer
2. 2
   Concentrationconcentrated

Procedure

To a solution containing Methyl 5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl) methyl]-2-furoate, 6, (15.1 g, 44 mmol) in MeOH (175 mL) and water (175 mL), a solution of NaOH (3.53 g, 88.3 mmol) in water (29 mL) was added. The reaction was stirred overnight at room temperature. After completion as judged by TLC, the solution was acidified with 1 M HCl to pH 2. The crude product was extracted in to organic layer using ethyl acetate and concentrated to afford 5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-2-furoic acid, 7 (15.0 g, 99% yield).

Source