Sodium Hydroxide → Benzenepropanol, 2-(hydroxymethyl)- (9CI)

HRID 1503393Notes

Reaction equation

HRID 1503393 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].C[O:12][C:13](=O)[CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18](OC)=[O:19].[OH-].[Na+]>CCOCC>[OH:19][CH2:18][C:17]1[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=1[CH2:15][CH2:14][CH2:13][OH:12]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 10353486HCID 10353486, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10419543Benzenepropanol, 2-(hydroxymethyl)- (9CI)Yield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of LAH (1.89 g, 49.77 mmol) in Et2O (40 mL) under N2 was cooled to 0° C. and was added AlCl3 (1.6 g, 11.8 mmol). The mixture was allowed to warm to room temperature and stirred for 30 minutes. A mixture of methyl 2-(3-methoxy-3-oxopropyl)benzoate (2 g, 9 mmol) in Et2O was added dropwise. The mixture was stirred overnight. Aqueous NaOH (1 N, 12 mL) was added at 0° C. The mixture was filtered and the cake was washed with EtOAc 3 times. The filtrate was dried and concentrated to give 3-(2-(hydroxymethyl)phenyl)propan-1-ol (1.46 g, 98%). 1H-NMR (CDCl3): 1.85 (m, 2H), 2.77 (m, 2H), 3.52 (m, 2H), 4.62 (s, 2H), 7.23 (m, 2H), 7.27 (m, 2H).

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred overnight
  3. filtrationThe mixture was filtered
  4. washthe cake was washed with EtOAc 3 times
  5. customThe filtrate was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f8acf49f46b64e47be8b05378cab6891
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

Loading…