Hydrochloric Acid → 2,4-Bis(benzyloxy)-5-isopropenylbenzoic acid

HRID 41390

Reaction equation

C([O:8][C:9](=[O:35])[C:10]1[CH:15]=[C:14]([C:16]([CH3:18])=[CH2:17])[C:13]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:12][C:11]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)C1C=CC=CC=1.[OH-].[Li+].Cl>C1COCC1.CO.O.O>[CH2:28]([O:27][C:11]1[CH:12]=[C:13]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:14]([C:16]([CH3:18])=[CH2:17])=[CH:15][C:10]=1[C:9]([OH:35])=[O:8])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2,4-bis-benzyloxy-5-isopropenyl-benzoic acid benzyl ester (40.8 g, 87.9 mmol) in THF-MeOH-water (3:1:1, 300 mL total) was added lithium hydroxide (8.42 g, 352 mmol). The mixture was heated at 50° C. for 16 h, allowed to cool to ambient and then diluted with water (300 mL). The mixture was taken to pH˜1 using conc. HCl (−30 mL) and then extracted with EtOAc (2×200 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered and reduced in vacuo. The solid residue was taken up in P.E-MeOH (9:1, 300 mL total), the slurry stirred for 1 h at ambient and the solid collected by filtration. The solid was dried in vacuo to give the title compound (26.8 g) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) 12.30 (s, 1H), 7.61 (s, 1H), 7.53 (d, J=7.0 Hz, 2H), 7.47-7.31 (m, 8H), 6.94 (s, 1H), 5.23 (d, J=14.0 Hz, 4H), 5.08 (d, J=9.0 Hz, 2H), 2.04 (s, 3H).

Workup

temperatureto cool to ambient and
extractionextracted with EtOAc (2×200 mL)
washThe combined organic extracts were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
filtrationcollected by filtration
customThe solid was dried in vacuo

Sources & evidence

ORD record: ord-1b2133e667754c7fa1d1e0eb664f0358
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530469B2

Linked notes

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