Sodium hydride → HCID 25056516, compound
Reaction equation
[CH2:1]([OH:5])[CH2:2][CH:3]=[CH2:4].Cl[CH2:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([OH:13])=[O:12].[H-].[Na+].CC(=C)COCC1C=C(C=CC=1)C(O)=O>>[CH2:1]([O:5][CH2:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([OH:13])=[O:12])[CH2:2][CH:3]=[CH2:4]Participants
5
Procedure
The reaction of But-3-en-1-ol and 3-chloromethyl-benzoic acid in the presence of sodium hydride was performed as described for Compound 37 to give 3-But-3-enyloxymethyl-benzoic acid as colorless oil. 1H-NMR (400 MHz, d6-DMSO): 7.89 (m, 1 arom.H); 7.84 (m, 1 arom.H); 7.54 (m, 1 arom.H); 7.47 (m, 1 arom.H); 5.80 (m, —CH═CH2); 5.06 (2 d-like, —CH═CH2); 4.61 (s, —OCH2—C6H4); 3.49 (m, CH2—CH—CH2CH2O); 2.31 (m, CH2═CH—CH2CH2O). 13C-NMR (100 MHz, d6-DMSO): 167.14 (—C═O); 139.11; 135.52; 131.72; 130.76; 128.54; 128.27; 128.10; 126.44; 71.17; 69.06; 33.70.
Sources & evidence
- ORD record
- ord-f22ec9a2363a4dfbbe422f7b2d5fadf5
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466199B2
Reaction notes
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