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

HRID 919113Notes

Reaction equation

HRID 919113 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-3e276ce1c7c5425b982a303dbcf8dc8b
Source dataset
uspto-grants-2016_03
Patent number
US09273003B2

Reaction notes

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