Hydrochloric Acid → HCID 12788291, compound

HRID 1660062Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[CH:24]1[CH2:29][C:28](=[O:30])[CH2:27][C:26](=[O:31])[CH:25]1C(OC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CCOCC.O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[CH:24]1[CH2:29][C:28](=[O:30])[CH2:27][C:26](=[O:31])[CH2:25]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-carbomethoxy-1,3-cyclohexanedione (20.8 g, 43.5 mmole), dioxane (40 ml) and 20% sodium hydroxide (40 ml) was heated at 100° C. for 2.5 hours. It was cooled in an ice bath and acidified with concentrated hydrochloric acid. This mixture was heated for one hour at 100° C., cooled to 0° C. and then neutralized with sodium bicarbonate. The resultant mixture was added to saturated sodium bicarbonate and ether. The ether extract was dried over magnesium sulfate and evaporated to an oil. Purification of this oil via column chromatography on one kg of silic gel eluted with 10% acetone-ether gave 10.9 g (60%) of the title compound.

Workup

temperatureIt was cooled in an ice bath
temperatureThis mixture was heated for one hour at 100° C.
temperaturecooled to 0° C.
extractionThe ether extract
dry with materialwas dried over magnesium sulfate
customevaporated to an oil
customPurification of this oil via column chromatography on one kg of silic gel
washeluted with 10% acetone-ether

Sources & evidence

ORD record: ord-1d6f03acc01c4648afb0b31506f513bb
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04306097

Reaction notes

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