Hydrochloric Acid → 4-[(4E)-3-(4-Carboxybenzyl)-5-(2-{4-[4-(trifluoromethyl)phenoxy]butoxy}phenyl)pent-4-en-1-yl]benzoic acid

HRID 1913802Notes

Reaction equation

C(C1[CH:46]=[CH:45][C:6]([CH2:7][CH:8](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=2)[CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=2)=[CH:5]C=1)#N.[OH-:47].[K+].Cl.[CH2:50]([OH:53])[CH2:51][CH3:52]>O>[C:50]([C:51]1[CH:46]=[CH:45][C:6]([CH2:7][CH:8](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][C:35]2[CH:36]=[CH:37][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:39][CH:40]=2)[CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=2)=[CH:5][CH:52]=1)([OH:47])=[O:53]

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of 450 mg (0.72 mmol) of methyl 4-[(4E)-3-(4-cyanobenzyl)-5-(2-{4-[4-(trifluoromethyl)phenoxy]butoxy}phenyl)pent-4-en-1-yl]benzoate in 15 ml of 1-propanol and 2 ml of water is mixed with 1207 mg (21.5 mmol) of potassium hydroxide and stirred at 110° C. for 12 h. After cooling, the mixture is acidified with 1 M hydrochloric acid, and the crystals which have separated out are filtered off with suction, washed several times with water and dried. 447 mg (0.65 mmol, 90% of theory, purity 92%) of the title compound are obtained.

Workup

temperatureAfter cooling
customthe crystals which have separated out
filtrationare filtered off with suction
washwashed several times with water
customdried

Sources & evidence

ORD record: ord-a5dfe1f4a375494ab7a3e9e088b94852
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609727B2

Reaction notes

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