Hydrochloric Acid → 5-Tert-butyl-2-methoxybenzoyl chloride

HRID 1824702Notes

Reaction equation

HRID 1824702 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[O:14][CH3:15].[OH-].[Na+].O.[ClH:20]>CO>[C:10]([C:8]1[CH:7]=[CH:6][C:5]([O:14][CH3:15])=[C:4]([CH:9]=1)[C:3]([Cl:20])=[O:2])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15724682Methyl 5-(tert-butyl)-2-methoxybenzoateHCID 23719242Sodium hydroxide--water (1/1/1)

Product 1

HCID 221431005-Tert-butyl-2-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3.8 g of 5-(tert-butyl)-2-methoxybenzoic acid methyl ester in MeOH (30 mL) was added 50% NaOH-water solution (1 mL). The resulting solution was stirred at room temperature for 3 hr. After the reaction was complete, the pH was adjusted to pH=2–3 using 1M HCl. The reaction mixture was collected by extraction with ethylacetate and water three times. The organic layer was dried over anhydrous magnesium sulfate (MgSO4) and evaporated under reduced pressure. After recrystallization, the final product yielded 3.4 g (96%). Without further purification a solution of 3.4 g of 5-(tert-butyl)-2-methoxybenzoic acid in 20 mL CH2Cl2 was slowly treated with SOCl2 (1.2 eq). The resulting solution was stirred at room temperature for 2 hr. The reaction mixture was evaporated under reduced pressure and dried in a vacuum oven overnight to yield 3.4 g (91.9%).

Workup

  1. customThe reaction mixture was collected by extraction with ethylacetate and water three times
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate (MgSO4)
  3. customevaporated under reduced pressure
  4. customAfter recrystallization

Sources & evidence

ORD record
ord-e8cd4a3a2227436c8f83a80cbdc0adba
Source dataset
uspto-grants-2006_05
Patent number
US07045520B2

Reaction notes

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