4-Hydroxybenzyl Alcohol → Butanoic acid, 4-[4-(hydroxymethyl)phenoxy]-, ethyl ester

HRID 1417765Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3][CH:4]=1

Participants

Reactant 4

HCID 1254-Hydroxybenzyl Alcohol

HCID 5238Sodium Iodide

HCID 11430Potassium Carbonate

HCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 22340602Butanoic acid, 4-[4-(hydroxymethyl)phenoxy]-, ethyl esterYield 90.1%

Procedure

4-Hydroxybenzyl alcohol (1 g, 8.06 mmol) is treated with 1.73 g (8.86 mmol) of ethyl 4-bromobutyrate, 3.34 g (24.2 mmol) of potassium carbonate and a catalytic amount (120 mg 0.81 mmol) of sodium iodide under the same conditions as described in Preparation 3 to give 1.73 g of 4-[4-(hydroxymethyl)phenoxy]butanoic acid, ethyl ester as a light brown oil (90%). The product is utilized in the next reaction without further purification. The 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (neat) 3400, 1730, 1610, 1580, 1510 cm-1 ; MS (CI) m/e 238, 221, 115.

Sources & evidence

ORD record: ord-ef24fbf27b5747179022e9af832ae1c7
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05877296

Reaction notes

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