Methanol → Methyl 4-hydroxy-3-(methoxymethyl)benzoate

HRID 219862Notes

Reaction equation

CO.[OH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[CH2:14][OH:15].[CH3:16]C1C=CC(S(O)(=O)=O)=CC=1>CCOC(C)=O>[OH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[CH2:14][O:15][CH3:16]

Participants

Conditions

Temperature: 130 °C

Procedure

To MeOH (100 mL) was added methyl 4-hydroxy-3-(hydroxymethyl)benzoate (10 g; 54.89 mmol; 1 eq.) and PTSA (1.89 g; 10.98 mmol; 0.20 eq.). The resulting suspension was heated to 130° C. for 1 hour. The reaction mixture was concentrated giving a yellow solid. It was dissolved in EtOAc (400 mL), washed with a saturated aqueous solution of NaHCO3 (200 mL), brine (200 mL), dried over MgSO4 and concentrated affording the title compound as an orange solid (9.59 g, 89%). 1H NMR (DMSO-d6, 300 MHz) δ 10.48 (br s, 1H), 7.87-7.86 (d, J=2.11 Hz, 1H), 7.76-7.28 (dd, J=8.44 Hz, 2.31 Hz, 1H), 6.91-6.88 (d, J=8.48 Hz, 1H), 4.39 (s, 2H), 3.79 (s, 3H), 3.33 (s, 3H). LC/MS (Method B): 195.2 (M−H)−.

Workup

concentrationThe reaction mixture was concentrated
customgiving a yellow solid
washwashed with a saturated aqueous solution of NaHCO3 (200 mL), brine (200 mL)
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-dc881d1e86d446d39332415cf14586e9
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202865B2

Reaction notes

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