4-Butoxybenzaldehyde → HCID 53992972, compound

HRID 610699Notes

Reaction equation

HRID 610699 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[CH2:28]([O:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1)[CH2:29][CH2:30][CH3:31]>C1COCC1>[CH2:28]([O:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[CH:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])=[CH:35][CH:34]=1)[CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 798134-ButoxybenzaldehydeHCID 161236(4-Carboxybutyl)triphenylphosphonium bromide

Product 1

HCID 53992972HCID 53992972, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was synthesized from 4-carboxybutyltriphenylphosphonium bromide (8.86 g, 20 mmol) and p-butoxybenzaldehyde (3.56 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Crystallization (petroleum ether) afforded the product (3.82 g, 73%) as white crystals (mp: 56-57° C.). IR: 3350-2500, 1700 cm-1 ; 1H-NMR: 1.00 (t, 3H), 1.50 (m, 2H), 1.80 (m, 4H), 2.40 (m, 4H), 3.90 (t, 2H), 5.50+6.00 (m, 1H), 6.38 (q, 1H), 7.05 (q, 4H), 11.00 (bs, 1H). Anal. Calcd. for C16H22O3 : C, 73.25, H, 8.45%; Found: C, 73.32, H, 84.6%. Z:E=37:63.

Workup

  1. customCrystallization (petroleum ether)

Sources & evidence

ORD record
ord-5f51d2f43bf34a4eb42cb5b91d223bd9
Source dataset
uspto-grants-1999_12
Patent number
US05998642

Reaction notes

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