2-Methylbenzoic acid → Ethyl 2-(4-hydroxybutyl)benzoate

HRID 1763690Notes

Reaction equation

HRID 1763690 reaction equation
[C:1]1(C)[C:2]([C:7](O)=[O:8])=C[CH:4]=[CH:5][CH:6]=1.[Li].[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:18][CH2:19][CH2:20]CCBr>C(O)C>[OH:8][CH2:7][CH2:2][CH2:1][CH2:6][C:5]1[CH:4]=[CH:17][CH:16]=[CH:15][C:14]=1[C:13]([O:18][CH2:19][CH3:20])=[O:12]

Participants

5

Reactant 3

HCID 83732-Methylbenzoic acidHCID 5590192-(4-Bromobutoxy)tetrahydro-2H-pyranHCID 3028194Lithium

Product 1

HCID 20310967Ethyl 2-(4-hydroxybutyl)benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound XIV is prepared by the following series of reactions. (1) o-Toluic acid is converted to its dianion with lithium diisoprpylamide; (2) the dianion is treated with 4-(tetrahydropyranyloxy)butyl bromide and the crude alkylate is heated with ethanol and a catalytic amount of mineral acid to yield ethyl 2-(4-hydroxybutyl)-benzoate; (3) the hydroxy ester in ether is treated with phosphorus tribromide to yield reagent XIV.

Sources & evidence

ORD record
ord-2e72602c57054455b9ad17a0bc25c5c9
Source dataset
uspto-grants-1978_09
Patent number
US04112236

Reaction notes

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