Sodium Hydroxide → 2-Methylpropyl 2-[[(3-methoxyphenyl)thio]methyl]-6-methylbenzoate

HRID 892205Notes

Reaction equation

HRID 892205 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([SH:11])[CH:8]=[CH:9][CH:10]=1.Br[CH2:13][C:14]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:15]=1[C:16]([O:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[O:17]>C(O)C(C)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([S:11][CH2:13][C:14]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:15]=2[C:16]([O:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[O:17])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 849893-MethoxybenzenethiolHCID 22241269HCID 22241269, compound

Product 1

HCID 222413382-Methylpropyl 2-[[(3-methoxyphenyl)thio]methyl]-6-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent2×

Procedure

A 10N solution of sodium hydroxide (0.32 mL, 3.2 mmol) is added slowly to a solution of 3-methoxybenzenethiol (0.42 g, 3.0 mmol) in isobutanol (2 mL) followed by a solution of isobutyl 2-bromomethyl-6-methyl-benzoate (0.96 g, 3.3 mmol, example 2) in isobutanol (2 mL). The reaction is allowed to stir 15 min and is then partitioned between ethyl acetate and dilute aqueous HCl. The organic phase is washed with water, dried over magnesium sulfate, concentrated and purified by column chromatography (silica, 40% dichloromethane in hexanes) to provide the title compound. MS (EI) 344 (M)+.

Workup

  1. customis then partitioned between ethyl acetate and dilute aqueous HCl
  2. washThe organic phase is washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. custompurified by column chromatography (silica, 40% dichloromethane in hexanes)

Sources & evidence

ORD record
ord-5e65aacdec9c47a0a4699199d45e5cc1
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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