3-Hydroxybenzaldehyde → 4-(3-Chloropropoxy)-M-anisaldehyde

HRID 1808748Notes

Reaction equation

HRID 1808748 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[O:10]=[CH:11][C:12]1[CH:20]=[CH:19][C:16]([O:17][CH3:18])=[C:14]([OH:15])[CH:13]=1.[O:21]=[CH:22][C:23]1[CH:31]=[CH:30][C:28]([OH:29])=[C:25]([O:26][CH3:27])[CH:24]=1.[OH:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH:36]=[O:37].Br[CH2:42][CH2:43][Cl:44]>>[Cl:44][CH2:11][CH2:12][CH2:20][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9].[Cl:44][CH2:43][CH2:42][CH2:27][O:26][C:25]1[CH:24]=[C:23]([CH:31]=[CH:30][C:28]=1[O:29][CH3:33])[CH:22]=[O:21].[Cl:44][CH2:43][CH2:42][CH2:18][O:17][C:16]1[CH:19]=[CH:20][C:12]([CH:11]=[O:10])=[CH:13][C:14]=1[O:15][CH3:1].[Cl:44][CH2:43][CH2:42][O:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH:36]=[O:37]

Participants

9

Reactant 5

HCID 1013-HydroxybenzaldehydeHCID 1183VanillinHCID 6998SalicylaldehydeHCID 78491-Bromo-2-ChloroethaneHCID 12127Isovanillin

Product 4

HCID 46108414-(3-Chloropropoxy)-M-anisaldehydeHCID 12793356HCID 12793356, compoundHCID 17620908HCID 17620908, compoundHCID 231438983-(3-Chloropropoxy)-4-methoxybenzaldehyde

Procedure

2-(3-chloropropoxy)benzaldehyde, 3-(3-chloropropoxy)-4-methoxybenzaldehyde and 4-(3-chloropropoxy)-3-methoxybenzaldehyde were prepared using corresponding aldehydes such as salicylaldehyde, isovanillin and vanillin. 3-(2-chloroethoxy)-benzaldehyde was prepared by treating 3-hydroxybenzaldehyde with 1-bromo-2-chloroethane using the similar method described above.

Sources & evidence

ORD record
ord-efb2bfa5c2c9405bac6ec90fa1e1f73e
Source dataset
uspto-grants-2013_01
Patent number
US08361996B2

Reaction notes

Loading…