Phenol → 6-(2-Pentyl-3,4-dichlorophenoxy)hexanoic acid

HRID 34974

Reaction equation

HRID 34974 reaction equation
[OH:1][CH:2]1[CH2:6][C:5]2C(Cl)=C(Cl)[CH:9]=[CH:10][C:4]=2[O:3]1.[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CC.[CH2:36]([C:41]1[C:46]([Cl:47])=[C:45]([Cl:48])[CH:44]=[CH:43][C:42]=1[OH:49])[CH:37]=[CH:38][CH2:39][CH3:40].C(C1C(Cl)=C(Cl)C=CC=1O)CCCC.C1(O)C=CC=CC=1.BrCCCCCC(O)=O>>[CH2:36]([C:41]1[C:46]([Cl:47])=[C:45]([Cl:48])[CH:44]=[CH:43][C:42]=1[O:49][CH2:9][CH2:10][CH2:4][CH2:5][CH2:6][C:2]([OH:3])=[O:1])[CH2:37][CH2:38][CH2:39][CH3:40]

Participants

7

Reactant 6

HCID 996PhenolHCID 202106-Bromohexanoic acidHCID 80374Propyltriphenylphosphonium bromideHCID 212972802-Pentyl-3,4-dichlorophenolHCID 212972952,3-Dihydro-2-hydroxy-4,5-dichlorobenzofuranHCID 544116102-(2-Pentenyl)-3,4-dichlorophenol

Product 1

HCID 212973066-(2-Pentyl-3,4-dichlorophenoxy)hexanoic acid

Procedure

Following the general procedure of Example 6B, 2.3 g. of 2,3-dihydro-2-hydroxy-4,5-dichlorobenzofuran and 17.3 g. of propyltriphenylphosphonium bromide were reacted to provide 840 mg. of 2-(2-pentenyl)-3,4-dichlorophenol which upon hydrogenation following the procedure of Example 6C provided 300 mg. of 2-pentyl-3,4-dichlorophenol. This phenol was then reacted with 5.1 mmoles of 6-bromohexanoic acid following the procedure of Example 1C to provide 58 mg. of the desired title product. NMR.

Workup

  1. customto provide 840 mg
  2. customprovided 300 mg
  3. customto provide 58 mg

Sources & evidence

ORD record
ord-bcfad02dc81843998440c27ff8dbbb80
Source dataset
uspto-grants-1988_08
Patent number
US04764521

Linked notes

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