Hydrochloric Acid → HCID 54088911, compound

HRID 1464816Notes

Reaction equation

HRID 1464816 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][OH:19])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.F[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1.Cl>O1CCCC1>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][O:19][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 145174-FluorobenzonitrileHCID 24758Sodium hydrideHCID 3017260p-(Benzyloxy)phenethyl alcohol

Product 1

HCID 54088911HCID 54088911, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

To a suspension of sodium hydride (60%, 2.2 g, 55 mmol) in dry tetrahydrofuran (250 ml) was added a solution of 1-benzyloxy-4-(2-hydroxyethyl)benzene (11.4 g, 50 mmol) in tetrahydrofuran (50 ml). The reaction was heated to 40° C. for 1 hour. 4-Fluorobenzonitrile (6.7 g, 55 mmol) was added and the mixture was heated to reflux for 5 hours, cooled and neutralized with concentrated HCl. The precipitate was filtered, the filtrate was concentrated to dryness and the resulting solid was recrystallized from ethanol (12 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 hours
  3. filtrationThe precipitate was filtered
  4. concentrationthe filtrate was concentrated to dryness
  5. customthe resulting solid was recrystallized from ethanol (12 g)

Sources & evidence

ORD record
ord-022cc61c3d534d348b1b2e71a915a0ef
Source dataset
uspto-grants-1994_04
Patent number
US05306726

Reaction notes

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