4-Propoxybenzaldehyde → HCID 54039598, compound

HRID 377485

Reaction equation

HRID 377485 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)[CH2:2][CH3:3].[Br-].[C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:16])=[O:15]>C1COCC1>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][C:14]([OH:16])=[O:15])=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 798124-PropoxybenzaldehydeHCID 2779280(5-Carboxypentyl)triphenylphosphanium bromide

Product 1

HCID 54039598HCID 54039598, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was synthesized from p-propoxybenzaldehyde (3.26 g, 20 mmol, prepared from 1-bromopropane and 4-hydroxybenzaldehyde) and 5-carboxypentyltriphenylphosphonium bromide (9.50 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Crystallization (petroleum ether) afforded the product (3.15 g, 60%) as white crystals (mp: 52-53° C.). IR: 3450-2500, 1730 cm-1 ; 1H-NMR: 1.00 (t, 3H), 1.48 (m, 2H), 1.67 (m, 2H), 1.82 (m, 2H), 2.35 (m, 4H), 3.92 (t, 2H), 5.72+6.05 (m, 1H), 6.35 (d, 1H), 7.05 (q, 4H), 10.40 (bs, 1H). Anal. Calcd. for C16H22O3 : C, 73.25, H, 8.45%. Found: C, 73.15, H, 8.45%. Z:E=30:70.

Workup

  1. customCrystallization (petroleum ether)

Sources & evidence

ORD record
ord-5544e728e3d54ce8ac043b0a7f203479
Source dataset
uspto-grants-2000_02
Patent number
US06025511

Linked notes

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