Butanal → Butylidene-5,6,7,8-tetrahydro-1,6,7-naphthalene triol

HRID 267558Notes

Reaction equation

HRID 267558 reaction equation
[OH:1][C@H:2]1[C@@H:11]([OH:12])[CH2:10][C:9]2[C:8]([O:13]C(C)(C)C(OCC)=O)=[CH:7][CH:6]=[CH:5][C:4]=2[CH2:3]1.[CH:22](=O)[CH2:23][CH2:24][CH3:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH:22](=[C:3]1[CH:2]([OH:1])[CH:11]([OH:12])[CH2:10][C:9]2[C:8]([OH:13])=[CH:7][CH:6]=[CH:5][C:4]1=2)[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 261ButanalHCID 6101p-Toluenesulfonic acidHCID 86733119cis-2-[(6,7-Dihydroxy-5,6,7,8-tetrahydro-1-naphthyl)oxy]-2-methylpropionic acid, ethyl ester

Product 1

HCID 131710089Butylidene-5,6,7,8-tetrahydro-1,6,7-naphthalene triol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3.6 g (0.02 moles) of the triol of Example 1 in 50 ml. of benzene, and 1.5 g of butanal in the presence of 0.1 g p-toluene sulfonic acid are mixed together and stirred for several hrs. Water is removed by azeotropic distillation and the residue is taken to dryness to yield 06, 07 -butylidene - 5,6,7,8-tetrahydro-1,6,7-naphthalene triol.

Workup

  1. customWater is removed by azeotropic distillation

Sources & evidence

ORD record
ord-bfef91a75d284b3fac20d1c446e50e07
Source dataset
uspto-grants-1976_03
Patent number
US03943149

Reaction notes

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