Ethanol → 2,3-Bis(benzyloxy)benzene-1,4-dicarboxylic acid

HRID 59182Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:23]([C:33]([O:35]CC2C=CC=CC=2)=[O:34])[CH:22]=[CH:21][C:10]=1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCO.O1CCOCC1.[Li+].[OH-]>O>[CH2:1]([O:8][C:9]1[C:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:23]([C:33]([OH:35])=[O:34])[CH:22]=[CH:21][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2 (56.970 g, 0.102 mol) was dissolved in 200 mL 1:1:EtOH:dioxane in a 1-L round-bottom flask, resulting in a dark orange, clear solution, to which a suspension of LiOH (7.315 g, 0.305 mol) in 75 mL water was added. The flask was fitted with a reflux condenser and magnetically stirred. The emulsion (containing undissolved LiOH) was heated to 60° C. for 12 h, and became a translucent, orange solution. The reaction mixture was filtered through a M glass frit, dissolved in 500 mL basic water, and washed with DCM (3×250 mL). The aqueous layer was acidifed with ˜80 mL conc. HCl, and the resulting white precipitate was filtered and washed with water. The solid was dried using house vacuum overnight, ground into a white powder, and dried on the vacuum line for 12 h (100%).

Workup

additionwas added
customThe flask was fitted with a reflux condenser
filtrationThe reaction mixture was filtered through a M glass frit
dissolutiondissolved in 500 mL basic water
washwashed with DCM (3×250 mL)
filtrationthe resulting white precipitate was filtered
washwashed with water
customThe solid was dried
customhouse vacuum overnight, ground
customdried on the vacuum line for 12 h (100%)

Sources & evidence

ORD record: ord-033705168c1d4f3c89b86b9027d3036a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09439984B2

Reaction notes

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