Hydrochloric Acid → 2-Butoxy-4-hydroxymethyl-benzoic acid methyl ester

HRID 424803Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][C:5]=1[O:12][CH2:13][CH2:14][CH2:15][CH3:16].[Li+].[OH-:19].Cl.[Si](C=[N+]=[N-])(C)(C)C.CCCCCC>CO.O.C1COCC1>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:19])=[CH:6][C:5]=1[O:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-bromomethyl-2-butoxy-benzoic acid methyl ester (0.0500 g, 1.67 mmol), THF (10 mL), H2O (10 mL), and LiOH (0.0160 g, 6.68 mmol) is stirred at 50° C. overnight. The mixture is acidified with 1.0 M HCl and the product is extracted with EtOAc (40 mL). The organic phase is washed with brine (20 mL) and dried (Na2SO4). After filtration, the filtrate is concentrated under reduced pressure to a residue. The residue is dissolved in CH2Cl2 (10 mL) and MeOH (10 mL) and treated with 2.0 M TMSCHN2 in hexane (5.0 mL, 10 mmol) at room temperature for 30 minutes. After concentration the residue is purified by flash chromatography to give 2-Butoxy-4-hydroxymethyl-benzoic acid methyl ester as a syrup (270 mg, 68%). LC-ES/MS: 239.3 (M+1).

Workup

extractionthe product is extracted with EtOAc (40 mL)
washThe organic phase is washed with brine (20 mL)
dry with materialdried (Na2SO4)
filtrationAfter filtration
concentrationthe filtrate is concentrated under reduced pressure to a residue
dissolutionThe residue is dissolved in CH2Cl2 (10 mL)
concentrationAfter concentration the residue
customis purified by flash chromatography

Sources & evidence

ORD record: ord-ccd59fd8226d41239bd7395c0af33219
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106077B2

Reaction notes

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