N,N-Dimethylformamide--water (1/1) → 3-(3-Hydroxyphenyl)-5-hexenoic acid

HRID 1662354Notes

Reaction equation

HRID 1662354 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([CH:12]2C(=O)OC(C)(C)[O:14][C:13]2=[O:21])[CH2:9][CH:10]=[CH2:11])[CH:5]=[CH:6][CH:7]=1.CN(C=O)C.O>CCOC(C)=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:9][CH:10]=[CH2:11])[CH2:12][C:13]([OH:21])=[O:14])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21962138N,N-Dimethylformamide--water (1/1)HCID 577059815-(1-(3-Hydroxyphenyl)-3-butenyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 577065823-(3-Hydroxyphenyl)-5-hexenoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 43.1 (3.4 g, 12 mmol) in 10:1 DMF/water (48 mL) was stirred overnight at 90° C. The mixture was cooled to room temperature, diluted with EtOAc, washed with 1 N HCl and brine, dried (MgSO4), and concentrated to afford 43.2 (2.4 g) as a pink oil. The crude product was used without further purification.

Workup

  1. washwashed with 1 N HCl and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d4cdf97db02c4a2cbb4e698ce8a40727
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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