Dimethyl 5-chloroisophthalate → Methyl 3-chloro-5-(hydroxymethyl)benzoate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[BH4-].[Na+]>CO.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH2:7][OH:8])[CH:11]=1)[C:12]([O:14][CH3:15])=[O:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of dimethyl 5-chloroisophthalate (10.0 g, 43.7 mmol, Astatech) in methanol (50 mL) and methylene chloride (50 mL) at 0° C. was added sodium borohydride (5.5 g, 140 mmol, Aldrich). The reaction was allowed to gradually reach room temperature and stir for 1 hour. Additional portions of sodium borohydride (0.50 g, 13 mmol) were added at 2 hours and 3 hours. The reaction mixture was cooled to 0° C. and the reaction was quenched with water. The layers were separated and the aqueous layer was extracted with three portions of DCM. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-25% EtOAc in hexanes. Yield: (4.51 g, 51%).
Workup
- customwas allowed to gradually reach room temperature
- customthe reaction was quenched with water
- customThe layers were separated
- extractionthe aqueous layer was extracted with three portions of DCM
- dry with materialThe combined organic extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe product was purified by flash chromatography
- washeluting with a gradient from 0-25% EtOAc in hexanes
Sources & evidence
- ORD record
- ord-12d76dd990a44861a9635243cd8208f8
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309246B2
Reaction notes
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