4-Hydroxybenzaldehyde → HCID 178472489, compound

HRID 1485097Notes

Reaction equation

HRID 1485097 reaction equation
OC1C=CC(C=O)=CC=1.BrCC1CCC1.[OH:16][CH:17]1[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]1.[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1>>[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][O:16][C@@H:17]2[CH2:18][CH2:19][C@H:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:22]2)=[CH:31][CH:30]=1.[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][O:16][C@H:17]2[CH2:18][CH2:19][C@H:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:22]2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 86973Ethyl 4-hydroxycyclohexanecarboxylateHCID 2734658(Bromomethyl)cyclobutane

Product 2

HCID 178472489HCID 178472489, compoundHCID 178472490HCID 178472490, compound

Procedure

Instead of 4-hydroxybenzaldehyde and (bromomethyl)cyclobutane, ethyl 4-hydroxycyclohexanecarboxylate (2.00 g) and 4-chlorobenzylbromide (2.86 g) were respectively used and treated by the same technique as in Reference Example 9-1 to give ethyl cis-4-[(4-chlorobenzyl)oxy]cyclohexanecarboxylate as a colorless oil (0.33 g) and ethyl trans-4-[(4-chlorobenzyl)oxy]cyclohexanecarboxylate as a pale yellow oil (0.47 g).

Workup

  1. additiontreated by the same technique as in Reference Example 9-1

Sources & evidence

ORD record
ord-aed76dc29433422586c1689c0fbca0d6
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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