p-Toluenesulfonic acid → Methyl 4-bromo-alpha-hydroxybenzeneacetate

HRID 718642

Reaction equation

HRID 718642 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.CC1C=CC(S(O)(=O)=O)=CC=1>CO>[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 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 97930p-Bromomandelic acid

Product 1

HCID 14571696Methyl 4-bromo-alpha-hydroxybenzeneacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2-(4-bromophenyl)-2-hydroxyacetic acid (5.0 g, 22 mmol) in MeOH (10 mL) was added 2,2-dimethoxypropane (3.4 g, 33 mmol) and 4-methylbenzene-1-sulfonic acid (2.0 mg, 0.010 mmol). The resulting solution was stirred overnight at 55° C. and allowed to cool to rt. The resulting mixture was concentrated under reduced pressure and poured into water (100 mL). The solids were collected by filtration and washed with hexanes (2×20 mL) to obtain compound 50a as a gray solid. 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. temperatureto cool to rt
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. additionpoured into water (100 mL)
  4. filtrationThe solids were collected by filtration
  5. washwashed with hexanes (2×20 mL)

Sources & evidence

ORD record
ord-f3e6ec73f897426aa199a0c9f89ac2fe
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Linked notes

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