3-Hydroxybenzaldehyde → o-(Allyloxy)benzaldehyde

HRID 2395000Notes

Reaction equation

HRID 2395000 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)CCl)[CH:2]=[CH2:3].[OH:13][C:14]1C=C(C=CC=1)C=O.C(Br)C=C.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:7][C:6]=1[CH:14]=[O:13])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 141693671-(Chloromethyl)-3-(2-propen-1-yloxy)benzene

Product 1

HCID 101335o-(Allyloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

c:- (A) 3-Allyloxybenzyl chloride was obtained as follows: A mixture of 3-hydroxybenzaldehyde (6 g), allyl bromide (6.25 g), and potassium carbonate (8.82 g) in DENT (30 ml) was stirred for 18 hours, poured into water (100 ml) and extracted with diethyl ether (3×150 ml). The combined organic extracts were washed with water (2×150 ml) and brine (2×150 ml), dried (magnesium sulphate) filtered and evaporated to give 2-allyloxybenzaldehyde (7.2 g).

Workup

  1. extractionextracted with diethyl ether (3×150 ml)
  2. washThe combined organic extracts were washed with water (2×150 ml) and brine (2×150 ml)
  3. dry with materialdried (magnesium sulphate)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-5d08afe52dd04e98ab1eb47281d3a941
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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