2-Bromohexanoic acid → Diphenylmethyl alpha-bromohexanoate

HRID 839456

Reaction equation

HRID 839456 reaction equation
[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH3:9])[C:3]([OH:5])=[O:4].[C:10]1([C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N+]=[N-])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH3:9])[C:3]([O:5][CH:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:4]

Participants

3

Reactant 2

HCID 120132-Bromohexanoic acidHCID 612301,1'-(Diazomethylene)bis(benzene)

Product 1

HCID 54027772Diphenylmethyl alpha-bromohexanoateYield 90%

Procedure

α-Bromohexanoic acid (1.95g) in light petroleum spirit (25ml, b.p. 40°-60° ) was treated with a stock solution of diphenyldiazomethane in petroleum spirit (b.p. 40°-60° ) (ca. 3.8 mmole/10ml) dropwise with stirring until a faint violet colour persisted. The mixture was stirred for 2 hours at room temperature, whereupon the solvent was removed in vacuo. The resulting oil in ethyl acetate was washed with a saturated aqueous solution of sodium bicarbonate then with water and dried. Removal of the solvent gave the title ester (3.0g, 90%), λmax (EtOH) 252, 258, 263.5, 267.5 and 276 nm (ε 1650, 1600, 1350, 1150 and 850).

Workup

  1. stirringThe mixture was stirred for 2 hours at room temperature, whereupon the solvent
  2. customwas removed in vacuo
  3. washThe resulting oil in ethyl acetate was washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialwith water and dried
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-d9d823cf3a1042729f2a024e02828cc1
Source dataset
uspto-grants-1978_06
Patent number
US04095021

Linked notes

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