2,2-Dimethoxypropane → Methyl 4-bromo-alpha-hydroxybenzeneacetate

HRID 1772603Notes

Reaction equation

HRID 1772603 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:13]OC(OC)(C)C>CO.CC1C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:12])[C:9]([O:11][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 97930p-Bromomandelic acid

Product 1

HCID 14571696Methyl 4-bromo-alpha-hydroxybenzeneacetateYield 75.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2-(4-bromophenyl)-2-hydroxyacetic acid (5.00 g, 21.6 mmol) in MeOH (10 mL) was added 2,2-dimethoxypropane (3.39 g, 32.6 mmol) and 4-methylbenzene-1-sulfonic acid (2.00 mg, 0.0100 mmol). The resulting solution was stirred at 55° C. overnight. The reaction mixture was concentrated under reduced pressure, and H2O (100 mL) was added. The resulting solids were collected by filtration and washed with hexane to obtain compound 9a as a gray solid (4.00 g, 72% yield). 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.54-7.51 (m, 2H), 7.35-7.28 (m, 2H), 5.18-5.16 (m, 1H), 3.793 (s, 3H), 3.51-3.49 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and H2O (100 mL)
  2. additionwas added
  3. filtrationThe resulting solids were collected by filtration
  4. washwashed with hexane

Sources & evidence

ORD record
ord-6cdccadcdc8c4eeba3c4ee9d9b9619c3
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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