Hydrochloric Acid → 7-Tert-butyl-chroman-4-ol

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[O:8][CH2:9][CH2:10][CH:11]1[O:16]CCCO1)([CH3:4])([CH3:3])[CH3:2].Cl>O1CCCC1.C(OCC)C>[C:1]([C:5]1[CH:6]=[C:7]2[C:17]([CH:11]([OH:16])[CH2:10][CH2:9][O:8]2)=[CH:18][CH:19]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

Procedure

The intermediate from step A was dissolved in 20 ml tetrahydrofuran. Concentrated hydrochloric acid (20 mL) was added, and the reaction mixture was stirred at ambient temperature for 4 hours, diluted with diethyl ether and washed with water. The isolated organic layer was dried with magnesium sulfate, filtered and the solvent removed under reduced pressure to give 2.87 g of crude 7-tert-butyl-chroman-4-ol which was used without further purification.