Water → 4-(2-Benzyloxyethyl)cyclohexanone

HRID 1393301Notes

Reaction equation

HRID 1393301 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[CH2:20][CH2:19][C:14]2(OCC[O:15]2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.CC1C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][C:14](=[O:15])[CH2:19][CH2:20]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 218796038-[2-(Benzyloxy)ethyl]-1,4-dioxaspiro[4.5]decane

Product 1

HCID 218796054-(2-Benzyloxyethyl)cyclohexanoneYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

8-(2-Benzyloxy-ethyl)-1,4-dioxa-spiro[4.5]decane (Intermediate R1, 1.02 g, 3.70 mmol) (obtainable as described in the publication by Ciufolini et. al. J. Amer. Chem. Soc. 1991, 113, 8016, incorporated herein by reference) was dissolved in acetone (100 mL):H2O (5 mL) and reacted with TsOH (140 mg, 0.74 mmol) at 45° C. for 5 h. After a standard aqueous work-up the material was purified by chromatography on SiO2 to give 4-(2-benzyloxy-ethyl)-cyclohexanone as a colorless oil (97%).

Workup

  1. customAfter a standard aqueous work-up the material was purified by chromatography on SiO2

Sources & evidence

ORD record
ord-018c1c302d664c12ae0296cc076c8556
Source dataset
uspto-grants-2008_03
Patent number
US07345077B2

Reaction notes

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