Dichloromethane → Hydrochloric Acid

HRID 1908104Notes

Reaction equation

HRID 1908104 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[C:16]([CH3:22])([CH3:21])[C:17]([O:19][CH3:20])=[O:18])[C:6]([O:8]C(C)(C)C)=[O:7].C(O)(C(F)(F)F)=O.C(Cl)[Cl:31]>>[ClH:31].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[C:16]([CH3:22])([CH3:21])[C:17]([O:19][CH3:20])=[O:18])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 58550749Tert-butyl 3-methoxy-4-(1-methoxy-2-methyl-1-oxopropan-2-yl)benzoate

Product 2

HCID 313Hydrochloric AcidHCID 585511353-Methoxy-4-(1-methoxy-2-methyl-1-oxopropan-2-yl)benzoic acid

Procedure

To the crude tert-butyl 3-methoxy-4-(1-methoxy-2-methyl-1-oxopropan-2-yl)benzoate from Step 2 was added DCM (1 mL) followed by TFA (540 μL, 7.0 mmol). The reaction was allowed to stir for 2 h before it was concentrated in vacuo. The residue was dissolved in DMF, filtered and was purified by prep-HPLC (MeOH:H2O, 1-99% in an HCl modifier) to give 3-methoxy-4-(1-methoxy-2-methyl-1-oxopropan-2-yl)benzoic acid. ESI-MS m/z calc. 252.1. found 253.2 (M+1)+; Retention time: 2.45 minutes (4 min run).

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe residue was dissolved in DMF
  3. filtrationfiltered
  4. customwas purified by prep-HPLC (MeOH

Sources & evidence

ORD record
ord-d98f5be3a03d452982d0b20a7eedeb5d
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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