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

HRID 2252372Notes

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 in 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 ppm 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 in vacuo
customThe product was triturated by ethyl ether

Sources & evidence

ORD record: ord-0492451a20284b06886c605a35e78349
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07321061B2

Reaction notes

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