4-Hydroxybenzyl Alcohol → Ethyl 2-(3,5-dimethylphenoxy)acetate

HRID 630628Notes

Reaction equation

HRID 630628 reaction equation
[C:1](O)(=O)[CH2:2][CH2:3]C#C.O[CH2:9]C1C=CC(O)=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:32]([O:35][CH2:36][CH3:37])(=[O:34])[CH3:33].[CH2:38]1[CH2:42][O:41][CH2:40][CH2:39]1>>[CH3:3][C:2]1[CH:1]=[C:42]([CH:38]=[C:39]([CH3:9])[CH:40]=1)[O:41][CH2:33][C:32]([O:35][CH2:36][CH3:37])=[O:34]

Participants

6

Reactant 5

HCID 1254-Hydroxybenzyl AlcoholHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 224644-Pentynoic acid

Product 1

HCID 7018365Ethyl 2-(3,5-dimethylphenoxy)acetateYield 40%

Procedure

Referring to FIG. 42, a mixture of pent-4-ynoic acid (1.10 g. 11.2 mmol), 4-(hydroxymethyl)phenol (1.40 g, 11.2 mmol) and DCC (3.5 g, 16.8 mmol) in THF (30 mL) was stirred at room temperature overnight. Ethyl acetate was added to dilute the mixture and the white solid was filtered off. The filtrate was collected and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=3:1 to 2:1) to afford compound 1 (0.91 g, 40% yield); 1H NMR (300 MHz, DMSO-d6): δ 7.35 (d, J=8.4 Hz, 2H), 7.06 (d, J=8.4 Hz, 2H), 5.23 (t, J=6.0 Hz, 1H), 4.49 (d, J=5.7 Hz, 2H), 2.90-2.89 (m, 1H), 2.81-2.76 (m, 2H), 2.55-2.50 (m, 2H).

Workup

  1. additionto dilute the mixture
  2. filtrationthe white solid was filtered off
  3. customThe filtrate was collected
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=3:1 to 2:1)

Sources & evidence

ORD record
ord-a1f6782e27954fb280d4e741b02bccf1
Source dataset
uspto-grants-2016_04
Patent number
US09315542B2

Reaction notes

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