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

HRID 1913803Notes

Reaction equation

C(C1C=[CH:42][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]([F:41])=[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][CH:4]=1)#N.[OH-:44].[K+].Cl.[CH2:47]([OH:50])[CH2:48][CH3:49]>O>[C:47]([C:48]1[CH:4]=[CH:5][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]([F:41])=[CH:37][CH:36]=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:42][CH:49]=1)([OH:50])=[O:44]

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of 460 mg (0.80 mmol) of methyl 4-[(4E)-3-(4-cyanobenzyl)-5-{2-[4-(4-fluorophenoxy)butoxy]phenyl}pent-4-en-1-yl]benzoate in 15 ml of 1-propanol and 2 ml of water is mixed with 1340 mg (23.89 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. 325 mg (0.52 mmol, 65% of theory, purity 93%) 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-d59c9dd5f65f42839eda4a23b2d36661
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609727B2

Reaction notes

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