1,4-Butanediol → 4-Tridecyloxybutanol

HRID 326104Notes

Reaction equation

HRID 326104 reaction equation
[Na].[CH2:2]([OH:7])[CH2:3][CH2:4][CH2:5][OH:6].Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>>[CH2:21]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:7])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9]

Participants

4

Reactant 3

HCID 80641,4-ButanediolHCID 130001-BromotridecaneHCID 5360545Sodium

Product 1

HCID 204623244-Tridecyloxybutanol

Conditions

Temperature
150 °C

Procedure

2.3 g. Sodium are dissolved by warming in 44 ml. butane-1,4-diol, 38 ml. 1-bromotridecane are added thereto and the reaction mixture is stirred for 5 hours at a bath temperature of 150° C. After cooling, extraction is carried out with a mixture of diethyl ether-ligroin (1:2 v/v), the extract is evaporated and the residue is purified on a silica gel column by elution with ligroin which is subsequently replaced by diethyl ether-ligroin (1:1 v/v). The desired fractions are collected and evaporated. 19.4 g. (71% of theory) of thin layer chromatographically uniform 4-tridecyloxybutanol are thus obtained; m.p. 26°-29° C.

Workup

  1. temperatureby warming in 44 ml
  2. temperatureAfter cooling
  3. extractionextraction
  4. additionis carried out with a mixture of diethyl ether-ligroin (1:2 v/v)
  5. customthe extract is evaporated
  6. customthe residue is purified on a silica gel column by elution with ligroin which
  7. customThe desired fractions are collected
  8. customevaporated

Sources & evidence

ORD record
ord-7885c4defce94df783299bf51313dffd
Source dataset
uspto-grants-1984_04
Patent number
US04444766

Reaction notes

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