Carbon Dioxide → 5-tert-Butyl-4-(2-methoxy-ethoxymethoxy)-2-methyl benzoic acid

HRID 356496Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:5]([O:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:4][C:3]=1[CH3:19].C([Li])CCC.[C:25](=[O:27])=[O:26].[OH-].[Na+]>C1COCC1.CCOCC>[C:8]([C:6]1[C:5]([O:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:4][C:3]([CH3:19])=[C:2]([CH:7]=1)[C:25]([OH:27])=[O:26])([CH3:11])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 1-bromo-5-tert-butyl-4-(2-methoxy-ethoxymethoxy)-2-methyl-benzene from Example ZZ (44.7 g, 135 mmol) in dry THF was cooled to -78° C. under nitrogen and treated with 1.6M n-butyllithium (93 mL, 149 mmol). The solution was stirred at -78° C. for 45 minutes and then poured over crushed dry ice. The mixture was allowed to warm to room temperature. Et2O (100 mL) and 2N NaOH (200 mL) were added; the organic layer was separated and re-extracted with 2N NaOH. The aqueous layers were combined, acidified to pH 2 with 6N HCl, and extracted with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated to give the title compound. 1H NMR (CDCl3) δ 1.35 (s, 9 H), 2.57 (s, 3 H), 3.37 (s, 3 H), 3.57 (m, 2 H), 3.81 (m, 2 H), 5.35 (s, 2 H), 6.98 (s, 1 H), 8.01 (s, 1 H).

Workup

customwas cooled to -78° C. under nitrogen
additionpoured
temperatureto warm to room temperature
customthe organic layer was separated
extractionre-extracted with 2N NaOH
extractionextracted with EtOAc
washThe combined organic extracts were washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-fb979cbab7ed41aa8ed19f5a0b6d9db9
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05834506

Reaction notes

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