Sodium Hydroxide → HCID 20462073, compound

HRID 326103Notes

Reaction equation

HRID 326103 reaction equation
[CH2:1]([SH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Na].[OH-:21].[Na+]>N1C=CC=CC=1>[CH2:1]([S:19][CH:2]([CH3:1])[CH2:3][CH2:4][OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86739374HCID 86739374, compound

Product 1

HCID 20462073HCID 20462073, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The starting material is obtained as follows: Butylene-1,3-glycol is reacted with acetic anhydride at ambient temperature to give butane-1,3-diol 1-acetate in a yield of 63% of theory. It is then esterified with benzenesulphochloride in the presence of pyridine and the reaction product is eluted over a silica gel column with diethyl ether-ligroin (1:1 v/v). There is obtained a yield of 24% of theory of a colourless oil which is reacted with sodium octadecanethiol in the manner described in Example 20B and then treated with a dilute aqueous solution of sodium hydroxide to give a yield of 12% of theory of 3-octadecylthiobutanol; m.p. 35°-38° C.

Workup

  1. washthe reaction product is eluted over a silica gel column with diethyl ether-ligroin (1:1 v/v)
  2. customThere is obtained a yield of 24% of theory of a colourless oil which

Sources & evidence

ORD record
ord-413b389702f342dfb4c873d192e3f9ff
Source dataset
uspto-grants-1984_04
Patent number
US04444766

Reaction notes

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