Acetone → Rac.-(e)-2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoic acid methyl ester

HRID 1058391Notes

Reaction equation

HRID 1058391 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5](=[O:24])[C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:22])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)=[CH:8][C:7]=1[Cl:23].CC(C)=O>CO>[CH3:3][O:4][C:5](=[O:24])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]([OH:22])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)=[CH:8][C:7]=1[Cl:23]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 23560779(E)-2-chloro-4-[3-(3-hydroxyphenyl)-1-oxoprop-2-en-1-yl]benzoic acid methyl ester

Product 1

HCID 23560777Rac.-(e)-2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoic acid methyl esterYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (25 mg, 0.66 mmol) was added to a solution of (E)-2-chloro-4-[3-(3-hydroxyphenyl)-1-oxoprop-2-en-1-yl]benzoic acid methyl ester (Example 91; 316 mg, 1 mmol) in methanol (3 mL). The solution was stirred at room temperature for 3 h, then acetone (1 mL) was added and the solution was stirred for a further 10 min. The solvent was evaporated, ethyl acetate (15 mL) was added and the solution was washed with 0.5N hydrochloric acid solution (10 mL) and brine. Each of the aqueous layers was extracted in turn with ethyl acetate (10 mL). The combined organic layers were dried (MgSO4), filtered, evaporated and the resulting solid was triturated with diethyl ether to furnish rac.-(E)-2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoic acid methyl ester (310 mg, 97% yield) as a colorless solid.

Workup

  1. stirringthe solution was stirred for a further 10 min
  2. customThe solvent was evaporated
  3. additionethyl acetate (15 mL) was added
  4. washthe solution was washed with 0.5N hydrochloric acid solution (10 mL) and brine
  5. extractionEach of the aqueous layers was extracted in turn with ethyl acetate (10 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customthe resulting solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-90f5dfbb0bac463badd3a6a306c18e3d
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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