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

HRID 1762234Notes

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-l-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-929e06584a7a4ae8ac3745349d163852
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04831059

Reaction notes

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