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3,4-dihydro-2H-pyran → Methyl 3-(2-tetrahydropyranyloxy)cyclohexanecarboxylate

HRID 1462921
Notes
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Reaction equation

HRID 1462921 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>CCOCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 12209242Methyl 3-hydroxycyclohexane-1-carboxylate

Product 1

HCID 13236238Methyl 3-(2-tetrahydropyranyloxy)cyclohexanecarboxylateYield 65.8%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl 3-hydroxycyclohexanecarboxylate [J. Am. Chem. Soc., 70, 1898 (1948)] (61 g) in ether (500 ml), 2,3-dihydropyran (49 g) and p-toluenesulfonic acid monohydrate (1 g) were added. The mixture was stirred at room temperature for 6 hours and washed with water and dried (MgSO4). The ether was distilled off, and the oily residue was distilled under reduced pressure to give methyl 3-(2-tetrahydropyranyloxy)cyclohexanecarboxylate (61.5 g, 60.2%, b.p. 120°-123° C./0.3 mmHg).

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. distillationThe ether was distilled off
  4. distillationthe oily residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-cd85fc058c144124b41814cf05302224
Source dataset
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04461902

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes