Hydrochloric Acid → 4-{(4E)-3-(4-Carboxybenzyl)-5-[2-({4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]benzyl}oxy)-phenyl]pent-4-en-1-yl}benzoic acid

HRID 1913801Notes

Reaction equation

HRID 1913801 reaction equation
C(C1C=[CH:47][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][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:46])([C:42]([F:45])([F:44])[F:43])[C:38]([F:41])([F:40])[F:39])=[CH:33][CH:32]=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-:49].[K+].Cl.[CH2:52]([OH:55])[CH2:53][CH3:54]>O>[C:52]([C:53]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][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:46])([C:38]([F:41])([F:39])[F:40])[C:42]([F:45])([F:43])[F:44])=[CH:33][CH:32]=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:47][CH:54]=1)([OH:49])=[O:55]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10311-PropanolHCID 14797Potassium HydroxideHCID 59180492Methyl 4-{(4E)-3-(4-cyanobenzyl)-5-[2-({4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]benzyl}-oxy)phenyl]pent-4-en-1-yl}benzoate

Product 1

HCID 162255814-{(4E)-3-(4-Carboxybenzyl)-5-[2-({4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]benzyl}oxy)-phenyl]pent-4-en-1-yl}benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 170 mg (0.25 mmol) of methyl 4-{(4E)-3-(4-cyanobenzyl)-5-[2-({4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]benzyl}oxy)phenyl]pent-4-en-1-yl}benzoate in 3 ml of 1-propanol and 2 ml of water is mixed with 427 mg (7.6 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. 135 mg (0.2 mmol, 79% of theory) of the title compound are obtained.

Workup

  1. temperatureAfter cooling
  2. customthe crystals which have separated out
  3. filtrationare filtered off with suction
  4. washwashed several times with water
  5. customdried

Sources & evidence

ORD record
ord-6e89c895220549bcb7b3c0ef16d539a6
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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