1-Hexanol → HCID 20040568, compound

HRID 1388205Notes

Reaction equation

HRID 1388205 reaction equation
[C:1]([C:5]1[C:10]([OH:11])=[CH:9][C:8]([C:12]([CH3:21])([CH3:20])[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:7]([OH:22])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:23](O)[CH2:24][CH2:25][CH2:26][CH2:27]C.C[O-].[Na+]>CCOCC>[C:1]([C:5]1[C:10]([OH:11])=[CH:9][C:8]([C:12]([CH3:21])([CH3:20])[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:17])=[C:7]([OH:22])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81031-HexanolHCID 10942334Sodium MethoxideHCID 20040641HCID 20040641, compound

Product 1

HCID 20040568HCID 20040568, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5 Parts of methyl 5-(4-t-butyl-2,5-dihydroxyphenyl)-5-methylhexanoate is converted to the corresponding n-hexyl ester after reaction with 20 parts n-hexanol and 0.25 part of sodium methoxide in a sealed glass tube for 7 days. The reaction mixture is diluted with ether, washed with dilute hydrochloric acid, then water, and stripped of ether and excess hexanol under reduced pressure to give a residue. Short-path distillation of the residue at 0.4 mb yields n-hexyl 5-(4-t-butyl-2,5-dihydroxyphenyl)-5-methyl-hexanoate [formula (125)] as an amber oil with the following percentage composition by weight:

Workup

  1. washwashed with dilute hydrochloric acid
  2. customto give a residue
  3. distillationShort-path distillation of the residue at 0.4 mb

Sources & evidence

ORD record
ord-298bd030b5cb4f63868dfe23dc967026
Source dataset
uspto-grants-1984_02
Patent number
US04430425

Reaction notes

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