4-Chlorobenzaldehyde → HCID 68089053, compound

HRID 712930Notes

Reaction equation

[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=1>>[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])=[CH:36][CH:35]=1

Participants

Reactant 2

HCID 77264-Chlorobenzaldehyde

HCID 18795071(9-Carboxynonyl)(triphenyl)phosphanium bromide

Product 1

HCID 68089053HCID 68089053, compound

Procedure

By the similar procedure of synthesis of B10, compound B2 (2.20 g, 4.28 mmol) and 4-chlorobenzaldehyde (401 mg, 2.85 mmole) were used as starting materials to afford B17 (526 mg, 1.77 mmol, 62%). mp: 93° C. 1H-NMR (CDCl3, 400 MHz) δ 7.21 (d, J=8.4 Hz, 1H), 7.08 (d, J=8.4 Hz, 2H), 2.54 (t, J=7.5 Hz, 2H), 2.33 (t, J=7.5 Hz, 2H), 1.53-1.63 (m, 4H), 1.26 (m, 12H). 13C-NMR (CDCl3, 100 MHz) δ 179.90, 141.28, 131.21, 129.71, 128.27, 35.26, 34.00, 31.35, 29.69, 29.44, 29.39, 29.36, 29.19, 29.13, 29.01, 24.64. HRMS (ESI) calculated for C17H25ClO2Na [M+Na]+: 319.1441, found: 319.1435.

Workup

customto afford B17 (526 mg, 1.77 mmol, 62%)

Sources & evidence

ORD record: ord-39457b552ac24b668dccf7ce7dfe2094
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181292B2

Reaction notes

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