Water → 7-Hydroxy-6-methoxy-1-tetralone
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13]C)[C:9](=[O:15])[CH2:8][CH2:7][CH2:6]2.O>CC(O)=O.Br>[OH:13][C:12]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:15])=[CH:4][C:3]=1[O:2][CH3:1]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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).
Workup
- extractionextracted with EtOAc
- dry with materialThe EtOAc layer was dried
- customevaporated to 12 g of crude product
- customPurification on 1200 g of silica gel eluting with 10% Et2O in CH2Cl2
Sources & evidence
- ORD record
- ord-621ac675adbd4667b8f184b2cac9b215
- Source dataset
- uspto-grants-2006_12
- Patent number
- USRE039419E1
Reaction notes
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