Dodecanal → Tert-butyl 3-hydroxytetradecanoate

HRID 1903521Notes

Reaction equation

HRID 1903521 reaction equation
[CH:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Br[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>[Zn]>[OH:13][CH:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 8194DodecanalHCID 79177tert-Butyl bromoacetate

Product 1

HCID 14247856Tert-butyl 3-hydroxytetradecanoateYield 80.7%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

The reaction of dodecanal (0.92 g) and tert-butyl bromoacetate (1.56 g) was carried out under the presence of zinc (0.59 g) according to similar manner to that of Preparation 1-(1) to afford an oil of tert-butyl 3-hydroxytetradecanoate (1.21 g).

Workup

  1. customof Preparation 1-(1)

Sources & evidence

ORD record
ord-483640d3b9a64d0e9e025bf81d86a151
Source dataset
uspto-grants-1984_03
Patent number
US04436726

Reaction notes

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