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Bromoform → [2-Chloro-3,4-bis-[(2-methoxy-ethoxy)-methoxy]-phenyl]-hydroxy acetic acid

HRID 2573
Notes
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Reaction equation

HRID 2573 reaction equation
[Cl-].[Li+].[OH-:3].[K+].[Cl:5][C:6]1[C:13]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:12]([O:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9].C(Br)(Br)Br.[O:32]1[CH2:37]COCC1>O>[Cl:5][C:6]1[C:13]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:12]([O:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[CH:11]=[CH:10][C:7]=1[CH:8]([OH:9])[C:37]([OH:32])=[O:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 5558Bromoform2×HCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 433294Lithium ChlorideHCID 183590912-Chloro-3,4-bis-[(2-methoxy-ethoxy)-methoxy]benzaldehyde

Product 1

HCID 18359099[2-Chloro-3,4-bis-[(2-methoxy-ethoxy)-methoxy]-phenyl]-hydroxy acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2.42 g of lithium chloride and 7.02 g of potassium hydroxide were dissolved in 30 ml of water at 0° C. and a solution of 10 g of 2-chloro-3,4-bis-[(2-methoxy-ethoxy)-methoxy] benzaldehyde (synthesized in Preparation 1), 2.8 ml of bromoform and 38 ml of dioxane were added to this mixture. The mixture was stirred for 24 hours at 0° C. and then another 2.8 ml of bromoform were added. The mixture stood for 16 hours and after dilution with 100 ml of water, the solution was washed with ether, decanted, cooled to 0° C. and acidified until the pH was 2.5-3. Extraction was carried out with ether and the organic phase was washed with water and dried. The solvent was driven off to collect 11.4 g of the desired product in the form of an oil with a Rf=0.1 [eluant: methylene chloride--methanol--acetic acid (89-10-1)].

Workup

  1. waitThe mixture stood for 16 hours
  2. washafter dilution with 100 ml of water, the solution was washed with ether
  3. customdecanted
  4. temperaturecooled to 0° C.
  5. extractionExtraction
  6. washthe organic phase was washed with water
  7. customdried
  8. customto collect 11.4 g of the desired product in the form of an oil with a Rf=0.1 [eluant: methylene chloride--methanol--acetic acid (89-10-1)]

Sources & evidence

ORD record
ord-30ada60bc0e74527b46c8f5abdf6a8c0
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728828

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes