Benzyl 3-Bromopropyl Ether → 3-(3-Benzyloxy-propoxy)-2-hydroxy-4-methyl-benzaldehyde

HRID 2368005Notes

Reaction equation

HRID 2368005 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[C:8]([CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:13][CH2:14][CH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC(C)([O-])C.[Na+]>CS(C)=O>[CH2:17]([O:16][CH2:15][CH2:14][CH2:13][O:10][C:9]1[C:2]([OH:1])=[C:3]([CH:6]=[CH:7][C:8]=1[CH3:11])[CH:4]=[O:5])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 2776064Benzyl 3-Bromopropyl EtherHCID 23676156Sodium t-butoxideHCID 537336632,3-Dihydroxy-4-methylbenzaldehyde

Product 1

HCID 866647413-(3-Benzyloxy-propoxy)-2-hydroxy-4-methyl-benzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Synthesized according to the methods of general procedure 4 in U.S. Pat. Pub. No. 20090227541 (U.S. patent application Ser. No. 12/142,692) using the following reactants and amounts: 2,3-dihydroxy-4-methyl-benzaldehyde (9 g, 59.21 mmol), (3-bromo-propoxymethyl)-benzene (11.5 mL, 65.13 mmol), sodium tert-butoxide (12.52 g, 130.26 mmol) and DMSO (100 mL). Purification: flash column chromatography (5-10% EtOAc/hexane): yield 15.1 g (85%). 1H NMR (400 MHz, CDCl3) δ (ppm): 11.05 (s, 1H), 9.84 (s, 1H), 7.38-7.26 (m, 5H), 7.20 (d, J=7.8 Hz, 1H), 6.80 (d, J=8.2 Hz, 1H), 4.55 (s, 2H), 4.15 (t, J=6.2 Hz, 2H), 3.73 (t, J=6.2 Hz, 2H), 2.31 (s, 3H), 2.19-2.00 (m, 2H).

Workup

  1. customSynthesized
  2. customPurification

Sources & evidence

ORD record
ord-cc12709ffc764a11834b93c03bc3b694
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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