Reaction #943988

Reaction equation

6,7-dimethoxy-1-tetralone

water

→

product

Yield 81.3%

7-Hydroxy-6-methoxy-1-tetralone

Yield 81.3%

Solvents

HOAc

HBr

Conditions

Workup

1. 1
   Extractionextracted with EtOAc
2. 2
   DryingThe EtOAc layer was dried
3. 3
   Otherevaporated to 12 g of crude product
4. 4
   OtherPurification on 1200 g of silica gel eluting with 10% Et2O in CH2Cl2

Procedure

A solution of 10 g (0.048 mole) of 6,7-dimethoxy-1-tetralone in 100 ml of HOAc and 100 ml of 48% aqueous HBr was heated at 95° C. for 7 hours. The reaction was cooled to room temperature and poured into water and extracted with EtOAc. The EtOAc layer was dried and evaporated to 12 g of crude product. Purification on 1200 g of silica gel eluting with 10% Et2O in CH2Cl2 gave 7.5 g of product. Mp 147-148° C. (literature mp 148-152° C., Journal of Organic Chemistry, 33, 1968, p. 508).

Source