Hydrochloric Acid → HCID 25149506, compound

HRID 2108641Notes

Reaction equation

HRID 2108641 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:26])[C:11]=1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([CH:23]([CH3:25])[CH3:24])[CH:14]=1)[C:5]([O:7]C)=[O:6].[OH-].[Na+].Cl>CO>[CH3:26][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([CH3:1])[C:11]=1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([CH:23]([CH3:24])[CH3:25])[CH:14]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25150125HCID 25150125, compound

Product 1

HCID 25149506HCID 25149506, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of methyl 3,5-dimethyl-4-(4′-methoxymethoxy-3′-iso-propylbenzyl)benzoate (0.750 g, 2.11 mmol) in MeOH (20.0 mL) at 0° C. was added 1 M NaOH (12.64 mL, 12.64 mmol). The reaction mixture was heated at 50° C. for 16 h, cooled to 0° C. and acidified with 2 N HCl. The mixture was extracted with ethyl acetate (20 mL) and washed with H2O (10 mL×2.). The solvent was removed under reduced pressure to afford 3,5-dimethyl-4-(4′-methoxymethoxy-3′-iso-propylbenzyl)benzoic acid as white solid (0.71 g, 98%): 1H NMR (300 MHz, DMSO-d6): δ 12.76 (s, 1 H), 7.65 (s, 2 H), 6.98 (m, 1 H), 6.91 (m, 1 H), 6.60 (m, 1 H), 5.17 (s, 2 H), 4.00 (s, 2 H), 3.37 (s, 3 H), 3.23 (m, 1 H), 2.27 (s, 6 H), 1.14 (d, J=6.0 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=hexanes-ethyl acetate (4:1); Rf=0.00.

Workup

  1. temperaturecooled to 0° C.
  2. extractionThe mixture was extracted with ethyl acetate (20 mL)
  3. washwashed with H2O (10 mL×2.)
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-add079387ab14629b0a5e5048f267860
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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