Sodium Hydroxide → 2-Chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoic acid

HRID 1058392Notes

Reaction equation

HRID 1058392 reaction equation
[OH-].[Na+].C[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]>CO.O1CCCC1>[Cl:23][C:7]1[CH:8]=[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:10]=[CH:11][C:6]=1[C:5]([OH:24])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23560777Rac.-(e)-2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoic acid methyl ester

Product 1

HCID 700297522-Chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoic acidYield 82.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

An aqueous solution of sodium hydroxide (1N, 3 mL, 3 mmol) was added to a solution of 2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoic acid methyl ester (Example 92; 310 mg, 0.97 mmol) in methanol/tetrahydrofuran (1:1; 6 mL). The solution was stirred at room temperature overnight and then evaporated to dryness. Water (4 mL) was added and the solution was acidified with 1N hydrochloric acid solution (3.3 mL). The mixture was stirred at room temperature for 1 h, then the solid was filtered off, washed with water and dried to afford 2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoic acid (243 mg, 82% yield) as an off-white solid.

Workup

  1. customevaporated to dryness
  2. additionWater (4 mL) was added
  3. stirringThe mixture was stirred at room temperature for 1 h
  4. filtrationthe solid was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-f28ab6d59d6f47b5aef43d8b70c964a1
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

Loading…