Hydrochloric Acid → p-Bromomandelic acid

HRID 1841640Notes

Reaction equation

HRID 1841640 reaction equation
[OH-:1].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:14])[CH:11](Cl)Cl)=[CH:6][CH:5]=1.Cl.C([O:18]CC)C>O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:14])[C:11]([OH:18])=[O:1])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 108908591-(4-Bromophenyl)-2,2-dichloroethan-1-one

Product 1

HCID 97930p-Bromomandelic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (72 g, 1.8 mol) is dissolved in 650 ml of water. The solution is heated to +60° C. and 1-(4-bromo-phenyl)-2,2-dichloro-ethanone (130 g, 0.48 mol) is added dropwise in order to control the reaction temperature not to exceed +65° C. After the addition is complete, stirring is continued for 1 hour at +60° C. The reaction mixture is then cooled to +15° C. and 95 ml of 10 N hydrochloric acid are added. Subsequently diethyl ether is added and the mixture is stirred vigorously for 30 minutes. The organic phase is separated and the aqueous layer is extracted twice with diethyl ether. The combined organic phases are washed with brine, dried over sodium sulfate and evaporated to yield (4-bromo-phenyl)-hydroxy-acetic acid. 1H-NMR (300 MHz, CDCl3): 4.95 (s, 1H, CHOH), 7.30 (d, 2H, CH arom.), 7.48 (d, 2H, CH arom.).

Workup

  1. temperatureThe solution is heated to +60° C.
  2. customto exceed +65° C
  3. additionAfter the addition
  4. temperatureThe reaction mixture is then cooled to +15° C.
  5. stirringthe mixture is stirred vigorously for 30 minutes
  6. customThe organic phase is separated
  7. extractionthe aqueous layer is extracted twice with diethyl ether
  8. washThe combined organic phases are washed with brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-5dcff7c2c80a438181359f7d149ca8f9
Source dataset
uspto-grants-2004_01
Patent number
US06683211B1

Reaction notes

Loading…