Hydrochloric Acid → [4-(3,4-Dichloro-benzyloxy)-phenyl]-hydroxy-acetic acid

HRID 2369112Notes

Reaction equation

HRID 2369112 reaction equation
ClC1C=C(C=CC=1Cl)C[O:6][C:7](=[O:26])[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)=[CH:12][CH:11]=1)[OH:9].[OH-].[Li+].Cl.CCOC(C)=O>C1COCC1.CO>[Cl:25][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[Cl:24])[CH2:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH:8]([OH:9])[C:7]([OH:26])=[O:6])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 669225903,4-Dichlorobenzyl 2-(4-((3,4-dichlorobenzyl)oxy)phenyl)-2-hydroxyacetate

Product 1

HCID 66923034[4-(3,4-Dichloro-benzyloxy)-phenyl]-hydroxy-acetic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2-[4-(3,4-Dichloro-benzyloxy)-phenyl]-2-hydroxy-acetic acid 3,4-dichloro-benzyl ester (9.4 g,) was dissolved in 120 mL of THF-methanol (4:1) and 2N lithium hydroxide solution (39 mL) added. The resulting reaction mixture was stirred at room temperature 16 h. The mixture was poured onto 1N HCl and EtOAc and the organic layer was washed with brine, dried over sodium sulfate, and concentrated. The residual oil was taken up in minimal DCM and hexanes added to give a solid. The solid was filtered and washed with hexanes to afford the desired product [4-(3,4-dichloro-benzyloxy)-phenyl]-hydroxy-acetic acid in pure form (6.1 g). 1H NMR (400 MHz, DMSO d6): 7.69 (d, 1H), 7.63 (d, 1H), 7.41 (m, 1H), 7.31 (m, 2H), 6.96 (m, 2H), 5.10 (s, 2H), 4.94 (s, 1H).

Workup

  1. customThe resulting reaction mixture
  2. washthe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. additionhexanes added
  6. customto give a solid
  7. filtrationThe solid was filtered
  8. washwashed with hexanes

Sources & evidence

ORD record
ord-b045e81650684864a4c2bd25ac5e7888
Source dataset
uspto-grants-2014_04
Patent number
US08703766B2

Reaction notes

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