Sodium Iodide → HCID 85809217, compound

HRID 964429Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:10][CH3:11].Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:3]([O:10][CH3:11])[CH:4]=1

Participants

Reactant 4

HCID 5238Sodium Iodide

HCID 11430Potassium Carbonate

HCID 62348Vanillyl alcohol

HCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 85809217HCID 85809217, compoundYield 47.1%

Procedure

4-Hydroxy-3-methoxybenzyl alcohol (1 g, 6.49 mmol) is treated with 1.73 g (7.13 mmol) of ethyl 4-bromobutyrate, 2.69 g (19.46 mmol) of potassium carbonate and a catalytic amount (97.22 mg 0.65 mmol) of sodium iodide as described in Preparation 3 to give 821 mg of 4-[4-(hydroxymethyl)-2-methoxyphenoxy]butanoic acid, ethyl ester as a light brown oil (47%). The 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (neat) 3500, 1730, 1620, 1600 cm-1 ; MS (CI (low res)) m/e 269 (M+H), 251, 223, 195.

Sources & evidence

ORD record: ord-06138ac622cd41f8969ca10afef07f78
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05767285

Reaction notes

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