4-Dodecyloxy-2-chlorobenzoic acid → 4-Dodecyloxy-2-chlorobenzyl alcohol

HRID 1650646Notes

Reaction equation

HRID 1650646 reaction equation
[CH2:1]([O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[C:16]([Cl:23])[CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[CH2:1]([O:13][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][OH:19])=[C:16]([Cl:23])[CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

3

Reactant 2

HCID 197388414-Dodecyloxy-2-chlorobenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 543889264-Dodecyloxy-2-chlorobenzyl alcohol

Procedure

According to customary procedures, 4-dodecyloxy-2-chlorobenzoic acid synthesized in the same manner as described in Referential Example 15 was reduced with LiAlH4 to obtain 4-dodecyloxy-2-chlorobenzyl alcohol, and this compound was brominated with PBr3 to obtain 4-dodecyloxy-2-chlorobenzyl bromide. In the same manner as described in Referential Example 18, 2.0 g of the so-obtained compound was reacted with 1.0 g of 4-acetoxyphenol to obtain 4-dodecyloxy-2-chlorobenzyl(4-acetoxyphenyl) ether. Then, the acetyl group was removed by an equimolar amount of LiOH, whereby 0.9 g of 4-dodecyloxy-2-chlorobenzyl(4-hydroxyphenyl) ether was obtained.

Workup

  1. customsynthesized in the same manner

Sources & evidence

ORD record
ord-37132dbda6bf422f8118ed0261d86571
Source dataset
uspto-grants-1990_05
Patent number
US04925591

Reaction notes

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