m-Chloroperbenzoic acid → 1-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-3-heptanone ethylene ketal

HRID 1650053Notes

Reaction equation

[CH2:1]1[O:33][C:4]2([CH2:9][CH2:8][CH:7]=[C:6]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([CH3:24])([CH3:23])[CH2:17]CCCCC)=[CH:12][C:11]=3[O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:5]2)[O:3][CH2:2]1.[C:34](=O)(O)[O-].[Na+].Cl[C:40]1[CH:45]=[CH:44]C=[C:42](C(OO)=O)[CH:41]=1>ClCCl>[CH2:2]1[O:3][C:4]([CH2:9][CH2:8][CH2:7][CH3:34])([CH2:5][CH2:6][C:10]2[CH:15]=[CH:14][C:13]([C:16]([CH3:24])([CH3:23])[CH2:17][CH2:42][CH2:41][CH2:40][CH2:45][CH3:44])=[CH:12][C:11]=2[O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[O:33][CH2:1]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 5.0 g. (11.2 mmole) of 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]cyclohex-3-en-1-one ethylene ketal in 15 ml. of dichloromethane is added 1.26 g. (15 mmole) of sodium bicarbonate and 2.58 g. (15 mmole) of m-chloroperbenzoic acid. The reaction is stirred overnight at 0° C. and then filtered. The filtrate is diluted with 200 ml. of ether and washed with two 100 ml. portions of saturated sodium bicarbonate. The organic extract is dried over magnesium sulfate and evaporated to yield the title compound.

Workup

customTo a 0° C.
filtrationfiltered
additionThe filtrate is diluted with 200 ml
washof ether and washed with two 100 ml
extractionThe organic extract
dry with materialis dried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-4ef89ef6d588462ebd7f296092be746f
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04921994

Reaction notes

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