Hydrochloric Acid → 3-[4-(Hydroxymethyl)phenyl]propanoic acid

HRID 475054Notes

Reaction equation

HRID 475054 reaction equation
C[CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[Li+].[OH-].Cl>CO.O>[OH:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:2][C:3]([OH:5])=[O:4])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67022307Methyl 3-[4-(hydroxymethyl)phenyl]propanoic acid

Product 1

HCID 203221243-[4-(Hydroxymethyl)phenyl]propanoic acidYield 98.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Intermediate B (5 g, 25.7 mmol) was dissolved in MeOH (50 mL) and water (10 mL). LiOH (1.85 g, 77.2 mmol) was added and the reaction stirred at RT for 18 h. The reaction mixture was acidified to pH˜3 with 1M HCl, the resulting precipitate was isolated by filtration to afford the desired product (4.57 g, quant.). 1H NMR (300 MHz, d6-DMSO) δ: 7.18 (4H, q), 4.45 (2H, d), 2.81 (2H, t), 2.62 (2H, t).

Workup

  1. customthe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-d915fee9eb9743618223db3af55640a1
Source dataset
uspto-grants-2014_01
Patent number
US08637547B2

Reaction notes

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