Water → 4-Benzo[1,3]dioxol-5-yl-4-hydroxycyclohexanone

HRID 274893Notes

Reaction equation

HRID 274893 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(OCC[O:14]4)[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.O>CC(C)=O.Cl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([OH:20])[CH2:11][CH2:12][C:13](=[O:14])[CH2:18][CH2:19]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 962WaterHCID 109128408-(Benzo[d][1,3]dioxol-5-yl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 151996894-Benzo[1,3]dioxol-5-yl-4-hydroxycyclohexanoneYield 95%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 8-(1,3-benzodioxol-5yl)-1,4-dioxaspiro[4.5]decan-8-ol (IIIb; 5 g, 18 mmole) in 75 ml acetone, 1 ml 12 N HCl, and 50 ml water, was stirred for 2 hr. After dilution with an additional 50 ml water the solid was collected to give the product (4.0 g, 95%, mp: 166°-168° C.).

Workup

  1. customAfter dilution with an additional 50 ml water the solid was collected

Sources & evidence

ORD record
ord-9b797b45feae49c982223b3f7a5feaff
Source dataset
uspto-grants-1995_02
Patent number
US05391570

Reaction notes

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