Hydrochloric Acid → Hydroxy(4-isopropylphenyl)acetic acid

HRID 1787084Notes

Reaction equation

HRID 1787084 reaction equation
[Cl-].[Li+].[OH-:3].[K+].C(Br)(Br)Br.[CH:9]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1)([CH3:11])[CH3:10].Cl.[O:21]1[CH2:26]COCC1>>[OH:17][CH:16]([C:15]1[CH:14]=[CH:13][C:12]([CH:9]([CH3:11])[CH3:10])=[CH:19][CH:18]=1)[C:26]([OH:21])=[O:3]

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 326CuminaldehydeHCID 5558BromoformHCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 433294Lithium Chloride

Product 1

HCID 23423233Hydroxy(4-isopropylphenyl)acetic acidYield 73%

Conditions

Temperature
7.5 °C

Procedure

To a mixture of lithium chloride (17.0 g, 418 mmol), potassium hydroxide (44.9 g, 800 mmol) and ice (150 g) was added a solution of bromoform (17.5 mL, 200 mmol) and 4-isopropyl benzaldehyde (30.3 mL, 200 mmol) in 1,4-dioxane (150 mL) at 0° C., and the mixture was stirred at 5-10° C. for 24 hours and then stirred at 35° C. for 24 hours. The aqueous layer was acidified with hydrochloric acid and was extracted with ethyl acetate. The extract was washed with water and then was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a residue, which was crystallized from hexane-ethyl acetate to obtain 28.5 g (yield 73%) of the title compound. Melting point: 156-157° C.

Workup

  1. stirringstirred at 35° C. for 24 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customto obtain a residue, which
  7. customwas crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-89b849bfcf45431dbc41fad8bbb3c08c
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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