Ammonium Chloride → 3-(4-HYDROXYMETHYL-PHENYL)-PROPAN-1-OL

HRID 2261436Notes

Reaction equation

HRID 2261436 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](O)=[O:18])=[CH:11][CH:10]=1.[NH4+].[Cl-]>C1COCC1>[OH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][OH:18])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 203221243-[4-(Hydroxymethyl)phenyl]propanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 112406973-(4-HYDROXYMETHYL-PHENYL)-PROPAN-1-OLYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To a suspension of LiAlH4 (155 mg, 4.0 mmol) in THF (25 mL) a solution of 3-(4-hydroxymethyl-phenyl)-propionic acid (720 mg, 4.0 mmol) in THF (20 mL) is added within 2 min. The resulting mixture is stirred at 70° C. for 80 min before it is treated with sat. aq. NH4Cl solution (10 mL). The suspension is filtered over celite, the filtrate is diluted with water (200 mL) and extracted with diethyl ether (2×75 mL) followed by EA (2×75 mL). The organic extracts are combined, dried over Na2SO4 and evaporated to leave 3-(4-hydroxymethyl-phenyl)-propan-1-ol (0.51 g) as a colourless oil; tR=0.61 min.

Workup

  1. additionis added within 2 min
  2. filtrationThe suspension is filtered over celite
  3. additionthe filtrate is diluted with water (200 mL)
  4. extractionextracted with diethyl ether (2×75 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-45526604902c4452b7c4006bf0946b1c
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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