Hydrochloric Acid → HCID 89690113, compound

HRID 714031Notes

Reaction equation

HRID 714031 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)=[CH:11][C:12]([CH2:33][CH3:34])=[C:13]([CH:32]=1)[O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[C:20]([CH2:29][CH2:30][CH3:31])=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22]([O:24]C)=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>CN1CCCC1=O.O.COC(C)(C)C>[CH2:1]([O:8][C:9]1[C:10]([C:35]2[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)=[CH:11][C:12]([CH2:33][CH3:34])=[C:13]([CH:32]=1)[O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[C:20]([CH2:29][CH2:30][CH3:31])=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22]([OH:24])=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 89690204HCID 89690204, compound

Product 1

HCID 89690113HCID 89690113, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of methyl 3-[3-[5-benzyloxy-2-ethyl-4-(4-fluorophenyl)phenoxy]propoxy]-2-propyl-benzoate (119 g, 181 mmol) in N-methylpyrrolidone (476 mL), add potassium hydroxide (21.2 g, 378 mmol) and stir 25 min at 120° C. Allow the mixture to cool and then dilute with water (240 mL) and methyl-tert-butylether (100 mL). Adjust to pH=2.5 with 12 N hydrochloric acid. Separate the phases and wash the aqueous phase with methyl-tert-butylether (3×35 mL). Wash the combined organic extracts twice with water and once with brine. Concentrate the organic extracts in vacuo. Recrystallize the resultant residue from acetonitrile, filter, and dry to yield (78 g, 67%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.60-7.47 (m, 3H); 7.37-7.20 (m, 6H); 7.12-7.02 (m, 4H); 6.60 (s, 1 H); 5.00 (s, 2H); 4.20 (m, 4H); 3.00 (m, 2H); 2.61 (q, J=7.7 Hz, 2H); 2.33 (m, 2H); 1.59 (m, 2H); 1.18 (t, J=7.7 Hz, 3H); 0.98 (t, J=7.7 Hz, 3H).

Workup

  1. temperatureAllow the mixture to cool
  2. customSeparate the phases
  3. washwash the aqueous phase with methyl-tert-butylether (3×35 mL)
  4. washWash the combined organic extracts twice with water
  5. concentrationConcentrate the organic extracts in vacuo
  6. customRecrystallize the resultant residue from acetonitrile
  7. filtrationfilter
  8. customdry
  9. customto yield (78 g, 67%) as a white solid

Sources & evidence

ORD record
ord-c3448b7ab093421f965d87101bb6b8d5
Source dataset
uspto-grants-2015_11
Patent number
US09187411B2

Reaction notes

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