Water → 4-(2-Benzyloxyethyl)cyclohexanone

HRID 2252946Notes

Reaction equation

HRID 2252946 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 desribed 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 EC 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-222ddbb102514411a07271e0242e7a48
Source dataset
uspto-grants-2008_01
Patent number
US07323485B2

Reaction notes

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