Lithium hydroxide, monohydrate → HCID 22684060, compound

HRID 1500975Notes

Reaction equation

HRID 1500975 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=1.O.[OH-].[Li+]>O1CCCC1.CO.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 28825877HCID 28825877, compound

Product 1

HCID 22684060HCID 22684060, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-((3-bromophenoxy)methyl)benzoate (1 g, 3.1 mmol) in tetrahydrofuran (30 mL) and methanol (10 mL) was added lithium hydroxide monohydrate (1.3 g, 31 mmol) in water (10 mL). The mixture was stirred at room temperature for 2 hours. The suspension was concentrated in vacuo and acidified with concentrated hydrochloride acid (12 N, 15 mL). Then the mixture was extracted with ethyl acetate (20 mL). The organic phase was separated and concentrated to give the product 4-((3-bromophenoxy)methyl)benzoic acid as a white solid (0.6 g, 63%). LRMS (M+H+) m/z: calcd 305.99. found 305. 1H NMR (300 MHz, d6-DMSO): δ 12.95 (s, 1H), 7.96 (d, J=8.4 Hz, 2H), 7.55 (d, J=8.4 Hz, 2H), 7.27-7.22 (m, 2H), 7.15-7.12 (m, 1H), 7.05-7.01 (m, 1H), 5.21 (s, 2H).

Workup

  1. concentrationThe suspension was concentrated in vacuo
  2. extractionThen the mixture was extracted with ethyl acetate (20 mL)
  3. customThe organic phase was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8b7c6b2a539342e695c2b41b92c39136
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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