Hydrochloric Acid → (2-Benzyloxy-phenyl) methanesulfonic acid

HRID 225980Notes

Reaction equation

[S:1]([O-:4])([O-:3])=[O:2].[Na+].[Na+].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21]Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][S:1]([OH:4])(=[O:3])=[O:2])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium sulfite (4.2 g) was added to a stirred mixture of 1-benzyloxy-2-bromomethyl-benzene (8.9 g), tetrabutylammonium iodide (59 mg) and water (150 ml). The mixture was warmed to reflux for overnight. As the mixture cooled to 0° C., it was acidified by 6N HCl. Extraction by ethyl acetate (100 ml×6) was performed (some remained in the aqueous layer). The combined organic phases were dried over MgSO4. The filtrate was concentrated on vacuo. The product was triturated by ethyl ether to give (2-Benzyloxy-phenyl)-methanesulfonic acid (678 mg, 8%). 1H NMR (400 MHz, DMSO-D6): δ 3.82 (s, 2 H) 5.09 (s, 2 H) 6.86 (t, J=7.45 Hz, 1 H) 6.96 (d, J=8.08 Hz, 1 H) 7.14 (t, J=7.83 Hz, 1 H) 7.32 (d, J=7.33 Hz, 1 H) 7.38 (t, J=7.33 Hz, 2 H) 7.46 (d, J=9.09 Hz, 1 H) 7.52 (d, J=7.07 Hz, 2 H).

Workup

temperatureThe mixture was warmed
temperatureto reflux for overnight
extractionExtraction by ethyl acetate (100 ml×6)
dry with materialThe combined organic phases were dried over MgSO4
concentrationThe filtrate was concentrated on vacuo
customThe product was triturated by ethyl ether

Sources & evidence

ORD record: ord-e4e4facb2d37421ab904aa5b8a69eba7
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557135B2

Reaction notes

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