Hydrochloric Acid → Methyl 4-Isopropyl-2-hydroxybenzoate

HRID 1787898Notes

Reaction equation

HRID 1787898 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([O:13]COC)[CH:5]=1)([CH3:3])[CH3:2].[C:17](Cl)(=O)C.Cl.C[Si](C=[N+]=[N-])(C)C>C(Cl)Cl.CO.CCCCCC>[CH:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:17])=[O:9])=[C:6]([OH:13])[CH:5]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 167693TrimethylsilyldiazomethaneHCID 685322784-Isopropyl-2-methoxymethoxybenzoic acid

Product 1

HCID 59745620Methyl 4-Isopropyl-2-hydroxybenzoate

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

The 4-isopropyl-2-methoxymethoxybenzoic acid (5.3 g, 23.6 mmol) was dissolved in methylene chloride (75 mL) and MeOH (75 mL). Acetyl chloride (1 mL) was added to generate HCl. The reaction mixture was stirred for 2 h. The reaction was washed with water (2×150 mL), dried (MgSO4), and concentrated under vacuum. The crude product was dissolved in methylene chloride (100 mL) and MeOH (30 mL) and to this solution a 2 M hexane solution of (trimethylsilyl)diazomethane (11.8 mL, 23.6 mmol) was added dropwise. After 1 h, the solvent was removed under vacuum, giving the title compound as an oil.

Workup

  1. washThe reaction was washed with water (2×150 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under vacuum
  4. dissolutionThe crude product was dissolved in methylene chloride (100 mL)
  5. waitAfter 1 h
  6. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-34d6ef1d399e470fa61f10610c2eca38
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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