Sodium Hydroxide → 2,3,6,7-Tetrahydrobenzo[1,2-b:4,5-b′]difuran-4-carboxylic acid
Reaction equation
[CH:1]([C:3]1[C:11]2[O:12][CH2:13][CH2:14][C:10]=2[CH:9]=[C:5]2[O:6][CH2:7][CH2:8][C:4]=12)=[O:2].[OH-:15].[Na+]>[Ag-]=O>[O:6]1[CH2:7][CH2:8][C:4]2=[C:3]([C:1]([OH:15])=[O:2])[C:11]3[O:12][CH2:13][CH2:14][C:10]=3[CH:9]=[C:5]12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
4-Formyl-2,3,6,7-tetrahydro-benzo[1,2-b; 4,5-b′]difuran (0.25 mmol; Lit.: A. P. Monte, D. Marona-Lewicka, M. A. Parker, D. B. Wainscott, D. L. Nelson, D. E. Nichols J. Med. Chem., 1996, 39, 2953-2961) is added to a stirred suspension of silver(I) oxide (0.375 mmol) in an aq. NaOH solution (5%, 0.20 mL). The mixture is stirred for 5 h, filtered and washed with water (2.0 mL). The filtrate is cooled to 0° C. and made acidic by dropwise addition of hydrochloric acid (25%). The obtained suspension is filtered off and washed with ice-cold water and heptane. The residue is dried in vacuo to give the desired acid as a grey powder which is used without further purification. LC-MS (basic): tR=0.20 min; [M−H]−=205.2.
Workup
- filtrationfiltered
- washwashed with water (2.0 mL)
- additionmade acidic by dropwise addition of hydrochloric acid (25%)
- filtrationThe obtained suspension is filtered off
- washwashed with ice-cold water and heptane
- customThe residue is dried in vacuo
Sources & evidence
- ORD record
- ord-39b077265da44ee9bfb5e87a1780b946
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08236801B2
Reaction notes
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