Hydrochloric Acid → 4-(1,3-Benzodioxol-5-yl)-4-methoxycyclohexanone

HRID 274895Notes

Reaction equation

HRID 274895 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([OH:20])[CH2:19][CH2:18][C:13]4([O:17]CCO4)[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.Cl.[CH3:22]O>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([O:20][CH3:22])[CH2:11][CH2:12][C:13](=[O:17])[CH2:18][CH2:19]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 109128408-(Benzo[d][1,3]dioxol-5-yl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 229240434-(1,3-Benzodioxol-5-yl)-4-methoxycyclohexanoneYield 70%

Procedure

A solution of 8-(1,3-Benzodioxol-5-yl)-1,4-dioxa-spiro[4.5]decan8-ol (5.0 g, 1.8 mmole) in 100 mL methanol with 1 mL conc. hydrochloric acid was stirred for 22 hr and the solution concentrated in vacuo. The residue was purified by chromatography on silica eluting with ethyl acetate-hexane (1:19) to give the product (70%, mp: 84°-85 ° C.).

Workup

  1. concentrationthe solution concentrated in vacuo
  2. customThe residue was purified by chromatography on silica eluting with ethyl acetate-hexane (1:19)

Sources & evidence

ORD record
ord-0fc48e1455e3459ebe6c2592c514e614
Source dataset
uspto-grants-1995_02
Patent number
US05391570

Reaction notes

Loading…