Lithium Hydroxide → HCID 22590982, compound

HRID 1844076Notes

Reaction equation

HRID 1844076 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13]C)=[O:12])[CH:2]=[CH2:3].[OH-].[Li+]>O1CCCC1.O>[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 10976292HCID 10976292, compound

Product 1

HCID 22590982HCID 22590982, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the Methyl 2-allylphenylacetate (Step 1, 0.400 mg. 2.10 mmol) in tetrahydrofurane (10 mL) was added Lithium hydroxide (0.097 g, 2.31 mmol) in water (10 mL). The solution was stirred at room temperature for 3 h and was concentrated in vacuo. Water (40 mL) was added and the pH was adjusted to 1. The solution was extracted with dichloromethane and the combined organic layers were dried and concentrated to give 2-allyl phenyl acetic acid (yellow oil, 363 mg, 98%); C11H12O2; MW: 176.22; ES− 175; IR 1702 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.16-7.38 (4H, m), 5.99 (1H, m), 5.11 (1H, m), 5.04 (1H, m), 3.73 (2H, s), 3.47 (2H, dt) ppm.

Workup

  1. concentrationwas concentrated in vacuo
  2. additionWater (40 mL) was added
  3. extractionThe solution was extracted with dichloromethane
  4. customthe combined organic layers were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f87428b2a7ac434a82a2cad467446924
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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