Isopropanol → Propan-2-yl (4-methoxyphenyl)acetate

HRID 420175Notes

Reaction equation

HRID 420175 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[CH:13](O)([CH3:15])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:13]([O:11][C:10](=[O:12])[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 76904-Methoxyphenylacetic AcidHCID 11776Triphenylphosphine

Product 1

HCID 230170Propan-2-yl (4-methoxyphenyl)acetateYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into an recovery flask, 16 mg (0.1 mmol) of 2-(4-methoxyphenyl)acetic acid, and 7 mg (0.1 mmol) of isopropanol were added, and dissolved in 5 ml of tetrahydrofuran. To this, 52 mg (0.2 mmol) of triphenylphosphine, and 177 mg (0.2 mmol) of the compound 14 of Example 8 were added, and stirred for 24 hours at room temperature. The solvent was distilled under a vacuum, acetonitrile was added, and filtration was carried out with an octadecylsilyl silica packed syringe, and from the filtrate, 16.7 mg of isopropyl-2-(4-methoxyphenyl)acetate was obtained. The yield was 70%.

Workup

  1. distillationThe solvent was distilled under a vacuum, acetonitrile
  2. additionwas added
  3. filtrationfiltration
  4. customwas carried out with an octadecylsilyl silica packed syringe

Sources & evidence

ORD record
ord-c058d985922f42cab15fd70406b2e89a
Source dataset
uspto-grants-2012_01
Patent number
US08093435B2

Reaction notes

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