Hydrochloric Acid → HCID 67606978, compound

HRID 2280849Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=1)=O.CC(C)([O-])C.[K+].[C:29]([O:37]C)(=[O:36])[CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33].Cl>O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=2)=[C:31]([C:32]([O:34][CH3:35])=[O:33])[CH2:30][C:29]([OH:37])=[O:36])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

Conditions

Temperature: 90 °C

Procedure

To a 2 L four-neck flask with overhead stirring was added the product from Step 1 (101 g), toluene (1.5 L) and potassium t-butoxide (50 g). Dimethyl succinate (60 mL) was added to the flask through addition funnel over 30 minutes. The reaction mixture was heated to 90° C. for 3 hours. The slurry was cooled and poured into ice water (1 L). The bottom water layer was acidified by hydrochloric acid (12N, 100 mL). The resulting slurry was extracted with ethyl acetate (1 L) and the top layer was washed with water and dried over sodium sulfate. The final solution was condensed to oily residue and the residue was dried in vacuum oven at 60° C. for 8 hours to afford 147 g of waxy solid, 4-(3,4-dimethoxyphenyl)-4-(4-t-butylphenyl)-3-methoxycarbonyl-3-butenoic acid. The product was used as is in next step without further purification.

Workup

temperatureThe slurry was cooled
extractionThe resulting slurry was extracted with ethyl acetate (1 L)
washthe top layer was washed with water
dry with materialdried over sodium sulfate
customcondensed to oily residue
customthe residue was dried in vacuum oven at 60° C. for 8 hours

Sources & evidence

ORD record: ord-fb100bcc898b459dbbce1eb36ef0f6ac
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139552B2

Reaction notes

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