Hydrochloric Acid → HCID 53703849, compound

HRID 906103Notes

Reaction equation

HRID 906103 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][C:4]=1[O:13][CH3:14].Cl.[OH2:16]>>[OH:16][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoate

Product 1

HCID 53703849HCID 53703849, compoundYield 35%

Procedure

methyl 4-(bromomethyl)-3-(methyloxy)benzoate (300 mg, 1.15 mmol) was suspended in water (3 ml) and concentrated aqueous hydrochloric acid (380 μl) was added. The reaction mixture was refluxed for 16 h, then cooled to room temperature and partitioned with ethyl acetate (10 ml). The organic phase was separated, washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography on silica gel (dichloromethane:methanol 95:5) to provide 4-(hydroxymethyl)-3-(methyloxy)benzoic acid (74 mg, 35% yield). MS (EI) for C9H10O4: 181(M−H).

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. custompartitioned with ethyl acetate (10 ml)
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel (dichloromethane:methanol 95:5)

Sources & evidence

ORD record
ord-d73a92cee6ba4ed0907fb57cce5b7e61
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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