Lithium hydroxide, monohydrate → HCID 86683438, compound

HRID 579473Notes

Reaction equation

HRID 579473 reaction equation
O[Li].O.[CH:4]([C:6]1[C:11]2[CH:12]=[C:13]([C:15]([O:17]CC)=[O:16])[O:14][C:10]=2[CH:9]=[CH:8][C:7]=1[OH:20])=[O:5]>O.C1COCC1>[CH:4]([C:6]1[C:11]2[CH:12]=[C:13]([C:15]([OH:17])=[O:16])[O:14][C:10]=2[CH:9]=[CH:8][C:7]=1[OH:20])=[O:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86683439HCID 86683439, compound

Product 1

HCID 86683438HCID 86683438, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The solution of LiOH—H2O (1.26 g, 60 mmol) in H2O (15 mL) was added dropwise to the solution of ethyl 4-formyl-5-hydroxybenzofuran-2-carboxylate (4.6 g, 20 mmol) in THF (40 mL). The reaction mixture was heated to 50° C. for 2 h. After cooled to RT, the reaction mixture was concentrated, then acidified with 3 M HCl to pH=2. The formed precipitate was filtered and washed with water, dried to give 4-formyl-5-hydroxybenzofuran-2-carboxylic acid (4.1 g. 87.8% yield). 1HNMR (DMSO, 400 MHz): δ 10.91 (s, 1H, OH), 10.47 (s, 1H, CHO); 7.92 (d, 1H, J=0.8 Hz, ArH), 70.87 (dd, 1H, J=9.2 Hz, 0.8 Hz, ArH), 7.13 (d, 1H, J=9.2 Hz, ArH); MS [ESI, MH+]: 207.1.

Workup

  1. temperatureAfter cooled to RT
  2. concentrationthe reaction mixture was concentrated
  3. filtrationThe formed precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2ffa5f7891a8458eaae5b36bed9a8aa6
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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